- Stereochemistry of organic sulfur compounds: More than 100?years of history, current state and further challenges
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In the paper presented are the author's subjective views on the most important achievements in the stereochemistry of organic sulfur compounds, which, as an object of research, has more than 100-year history. Prospects for further development are also men
- Drabowicz, Józef
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- Efficient Synthesis of Sulfinate Esters and Sulfinamides via Activated Esters of p -Toluenesulfinic Acid
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Sulfinate esters were prepared by the process of activating p -toluenesulfinic acid with either cyanuric chloride, methanesulfonyl chloride, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl). Activation of p -toluenesulfinic acid with cyanuric chloride led to the formation of sulfinate esters that were accompanied by the formation of the corresponding sulfones. The use of methanesulfonyl chloride for activation via methanesulfonic p -toluenesulfinic anhydride afforded mixtures of sulfinate esters and methanesulfonates. The use of the carbodiimide EDC proved to yield the best results with the highly selective formation of the target sulfinate esters. The use of trimethylacetic p -toluenesulfinic anhydride or cyanuric chloride to achieve the synthesis of sulfinamides proved to be ineffective due to poor chemoselectivity of the nucleophilic attack on the activated p -toluenesulfinic acid anhydride. Ultimately, the use of EDC-HCl to form the sulfinamides proved to be the best pathway for synthesis.
- Gafur, Sayed Habibul,Waggoner, Stephanie L.,Jacobsen, Eric,Hamaker, Christopher G.,Hitchcock, Shawn R.
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- N - P -Toluenesulfinylimidazole: A New in situ Reagent for the Mild and Efficient Synthesis of p -Toluenesulfinate Alkyl Esters and Aryl Esters
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A new synthetic methodology has been developed for the synthesis of sulfinate alkyl and aryl esters. The methodology involves the combination of p -toluenesulfinic acid and 1,1′-carbonyldiimidazole (CDI) to create the putative reagent sulfinylimidazole. The process spontaneously releases carbon dioxide upon the addition of the CDI to the acid suggesting the rapid formation of the proposed reagent. Reaction of this reagent with a series of alcohols (primary, secondary, and tertiary) afforded the corresponding sulfinate alkyl esters in good to excellent yields by the addition of alcohols. It was also possible to form the related sulfinate aryl esters by treating the proposed sulfinylimidazole with selected phenols (phenol, p - tert -butylphenol, and thymol). The aryl esters were formed in excellent conversion based on analysis of the 500 MHz 1H NMR spectra of the crude reaction mixtures.
- Shaw, Jessica L.,Austermuehle, Brad J.,Witte, Jordan M.,Dorsey, Timothy R.,Delach, Christina,Hamaker, Christopher G.,Hitchcock, Shawn R.
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supporting information
p. 2693 - 2701
(2021/04/27)
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- Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism
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Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.
- Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
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p. 1846 - 1855
(2019/02/14)
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- Two Stereoinduction Events in One C?H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes
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Herein we disclose the synthesis of original chiral scaffolds—ortho-orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C?H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo-stereoselective C?H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho-terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N-Biax and diphosphine BiaxPhos.
- Dherbassy, Quentin,Djukic, Jean-Pierre,Wencel-Delord, Joanna,Colobert, Fran?oise
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supporting information
p. 4668 - 4672
(2018/03/21)
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- Palladium-Catalyzed Enantioselective C?H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization
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The first example of PdII-catalyzed enantioselective C?H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) throu
- Zhu, Yu-Chao,Li, Yan,Zhang, Bo-Chao,Zhang, Feng-Xu,Yang, Yi-Nuo,Wang, Xi-Sheng
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supporting information
p. 5129 - 5133
(2018/03/27)
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- A mixed anhydride approach to the preparation of sulfinate esters and allylic sulfones: Trimethylacetic p-toluenesulfinic anhydride
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A reagent combination of toluenesulfinic acid and trimethylacetyl chloride affords a putative trimethylacetic p-toluenesulfinic anhydride. This reagent has been used to prepare a series of sulfinate esters from primary and secondary alcohols. In addition, the reagent was used to convert Baylis-Hillman substrates into allylic sulfones. Attempts to use the reagent to convert amines to sulfinamides were unsuccessful. In contrast, the use of 2-pyrrolidinone afforded N-p-toluenesulfinyl pyrrolidinone in 64% yield. The use of a chiral 4-benzyl-1,3-oxazolidinone or 4-benzyl-1,3-oxazolidine-2-thione led to the isolation of S-p-tolyl p-toluenethiosulfonate.
- Jacobsen, Eric,Chavda, Mihir K.,Zikpi, Kokou M.,Waggoner, Stephanie L.,Passini, Daniel J.,Wolfe, Jesse A.,Larson, Robert,Beckley, Chelsea,Hamaker, Christopher G.,Hitchcock, Shawn R.
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supporting information
p. 3073 - 3077
(2017/07/17)
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- Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates
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Two simple and efficient methods for the synthesis of sulfinate esters and thiosulfonates from sodium salts of sulfinic acids are described. Different alcohols were converted into the corresponding sulfinate esters in good yields and purity in an open flask. By the adjustment of the reaction conditions thiosulfonates could also be obtained in a very short reaction time.
- Tranquilino, Arisson,Andrade, Silvia R.C.P.,da Silva, Ana Paula M.,Menezes, Paulo H.,Oliveira, Roberta A.
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supporting information
p. 1265 - 1268
(2017/03/10)
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- Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization
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A full account of our efforts toward an asymmetric redox bicycloisomerization reaction is presented in this article. Cyclopentadienylruthenium (CpRu) complexes containing tethered chiral sulfoxides were synthesized via an oxidative [3 + 2] cycloaddition reaction between an alkyne and an allylruthenium complex. Sulfoxide complex 1 containing a p-anisole moiety on its sulfoxide proved to be the most efficient and selective catalyst for the asymmetric redox bicycloisomerization of 1,6- and 1,7-enynes. This complex was used to synthesize a broad array of [3.1.0] and [4.1.0] bicycles. Sulfonamide- and phosphoramidate-containing products could be deprotected under reducing conditions. Catalysis performed with enantiomerically enriched propargyl alcohols revealed a matched/mismatched effect that was strongly dependent on the nature of the solvent.
- Trost, Barry M.,Ryan, Michael C.,Rao, Meera
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p. 1136 - 1152
(2016/07/06)
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- Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach
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A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).
- Kadari, Lingaswamy,Radha Krishna, Palakodety,Lakshmi Prapurna
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supporting information
p. 3863 - 3868
(2016/12/16)
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- Synthesis of axially chiral biaryls through sulfoxide-directed asymmetric mild C-H activation and dynamic kinetic resolution
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A mild and robust direct C-H functionalization strategy has been applied to the synthesis of axially chiral biaryls. Such an efficient and stereoselective transformation occurs through an original dynamic kinetic resolution pathway enabling the conversion of diastereomeric mixtures of non-prefunctionalized substrates into atropisomerically pure, highly substituted biaryl scaffolds. The main feature of this transformation is the use of an enantiopure sulfoxide as both chiral auxiliary and traceless directing group. The potential of newly synthesized biaryls as valuable building blocks is further illustrated.
- Hazra, Chinmoy Kumar,Dherbassy, Quentin,Wencel-Delord, Joanna,Colobert, Franoise
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supporting information
p. 13871 - 13875
(2015/03/04)
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- A chiral sulfoxide-ligated ruthenium complex for asymmetric catalysis: Enantio- and regioselective allylic substitution
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The design and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols with good regio- and enantioselectivities.
- Trost, Barry M.,Rao, Meera,Dieskau, Andre P.
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supporting information
p. 18697 - 18704
(2014/01/06)
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- Preparation and reactions of enantiomerically pure α-functionalized grignard reagents
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A strategy for the generation of enantiomerically pure α- functionalized chiral Grignard reagents is presented. The approach involves the synthesis of α-alkoxy and α-amino sulfoxides in ≥99:1 dr and ≥99:1 er via asymmetric deprotonation (s-BuLi/chiral diamine) and trapping with Andersen's sulfinate (menthol derived). Subsequent sulfoxide → Mg exchange (room temperature, 1 min) and electrophilic trapping delivers a range of enantiomerically pure α-alkoxy and α-amino substituted products. Using this approach, either enantiomer of products can be accessed in 99:1 er from asymmetric deprotonation protocols without the use of (-)-sparteine as the chiral ligand. Two additional discoveries are noteworthy: (i) for the deprotonation and trapping with Andersen's sulfinate, there is a lack of stereospecificity at sulfur due to attack of a lithiated intermediate onto the α-alkoxy and α-amino sulfoxides as they form, and (ii) the α-alkoxy-substituted Grignard reagent is configurationally stable at room temperature for 30 min.
- Rayner, Peter J.,O'Brien, Peter,Horan, Richard A. J.
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supporting information
p. 8071 - 8077
(2013/07/11)
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- Atropodiastereoselective C-H olefination of biphenyl p-tolyl sulfoxides with acrylates
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A stereoselective method for the synthesis of axially chiral biaryl scaffolds by C-H bond functionalization was accomplished using chiral sulfoxide both as the directing group enabling the regioselective activation of a C-H bond and as the chiral auxiliary generating an asymmetric environment in the coordination sphere of the metal complex. We have demonstrated the directing ability of the p-tolylsulfinyl group in promoting the Pd(II)-catalyzed C-H olefination of biphenyls.
- Wesch, Thomas,Leroux, Frederic R.,Colobert, Franoise
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supporting information
p. 2139 - 2144
(2013/10/01)
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- Structure elucidation and stereoselective total synthesis of pavettamine, the causal agent of gousiekte
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The structure elucidation of a novel natural product pavettamine (1), the causal agent of the plant toxicosis gousiekte, is reported. The structure was defined by analysis of NMR and MS data and the relative configuration followed from the 13C NMR data of the acetonide derivative. The absolute stereochemistry was established by total synthesis from (2S)-malic acid using chiral sulfoxide methodology as (2S,4R,8R,10S)-1,11-diamino-6-aza-undecane-2,4,8,10-tetraol.
- Bode, Moira L.,Gates, Paul J.,Gebretnsae, Samson Y.,Vleggaar, Robert
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supporting information; experimental part
p. 2026 - 2036
(2010/04/26)
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- NEW COMPOUNDS FOR THE TREATMENT OF CANCER
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The invention provides a method of preparing the stereoisomers of 1,11-diamino-6-aza- undecane-2,4,8,10-tetraol.
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Page/Page column 19-20
(2009/12/28)
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- An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions
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The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.
- Hajipour, Abdol R.,Falahati, Ali R.,Ruoho, Arnold E.
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p. 2717 - 2719
(2007/10/03)
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- Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids
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Putative enantioenriched carbenoid species, (R)-1-chloro-2- phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(Rs,R)-1- chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.
- Blakemore, Paul R.,Marsden, Stephen P.,Vater, Huw D.
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p. 773 - 776
(2007/10/03)
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- Synthesis of nonracemic α-trifluoromethyl α-amino acids from sulfinimines of trifluoropyruvate
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We describe a novel and useful method for the synthesis of nonracemic α-trifluoromethyl α-amino acids (α-Tfm-AAs). Key building blocks are the sulfinimines (S)-1a and (S)-1b, prepared by Staudinger reaction from trifluoropyruvate esters and the chiral N-sulfinyl iminophosphorane (S)-8, which were treated with benzyl, allyl, and alkylmagnesium halides. The resulting diastereomeric N-sulfinyl α-Tfm α-amino esters, 12 and 13, were produced with moderate to good stereoselectivity and yields. When alkyl Grignard reagents were used, stereocontrol became progressively higher with increasing steric bulk, while reversed, though poor, stereocontrol was achieved with benzyl/allyl Grignard reagents. An explanation for the observed stereochemical outcome is proposed, on the basis of the exclusive E geometry (N-sulfinyl and CF3 trans about the C=N bond) of the chiral sulfinimines 1. This assignment is the product of structural correlation and is supported by ab initio calculations and NOE experiments. Sulfinamides 12 and 13 were transformed into a series of nonracemic α-Tfm-AAs 16-22. The sulfinyl auxiliary can be regenerated and recycled.
- Asensio, Amparo,Bravo, Pierfrancesco,Crucianelli, Marcello,Farina, Alessandra,Fustero, Santos,Soler, Juan García,Meille, Stefano V.,Panzeri, Walter,Viani, Fiorenza,Volonterio, Alessandro,Zanda, Matteo
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p. 1449 - 1458
(2007/10/03)
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- Organic reactions under solid-state conditions
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Manipulatively simple and rapid methods are described for the synthesis of: chiral sulfinate esters from sulfonyl chlorides and sufonic acids; aldehydes and ketones from oximes, alcohols, hydrozones; sulfoxides from sulfides; and disulfides from thiols. The chemical yields are good to excellent and diastereoselectivity is high.
- Hajipour,Mallakpour
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p. 371 - 387
(2007/10/03)
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- Highly diastereoselective synthesis and easy method for synthesis of optically active sulfinate esters from aromatic disulfides
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One-step synthesis of chiral aromatic sulfinate esters 2 from aromatic disulfides 1 using lead tetraacetate is reported. The yields are good to excellent and diastereoselectivity is high.
- Hajipour,Islami
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p. 536 - 538
(2007/10/03)
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- A convenient and mild procedure for the synthesis of alkyl p- toluenesulfinates under solvent-free conditions using microwave irradiation
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The reactions of aliphatic alcohols with p-toluenesulfinic acid are accelerated by microwave irradiation under solvent-free conditions in the presence of silica gel to afford a high yielding synthesis of p- toluenesulfinate esters.
- Hajipour, Abdol R.,Mallakpour, Shadpour E.,Afrousheh, Aboulfazl
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p. 2311 - 2316
(2007/10/03)
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- An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine
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An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphos
- Watanabe, Yoshihiko,Mase, Nobuyuki,Tateyama, Moto-Aki,Toru, Takeshi
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p. 737 - 745
(2007/10/03)
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- A convenient and highly diastereoselective synthesis of optically active sulfinate esters from sulfonyl chlorides under solid state conditions
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A manipulatively simple and rapid method for synthesis of chiral sulfinate esters 1 and 2 from sulfonyl chloride and trimethyl phosphite in solid phase conditions supported on silica gel is described. The chemical yields are good to excellent and diastereoselectivity is high.
- Hajipour, Abdolreza,Islami, Fereshteh
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p. 461 - 462
(2007/10/03)
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- Enantioselective synthesis of haminol-1, an alarm pheromone of a Mediterranean mollusc
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The first enantioselective synthesis of (-)-(R)-haminol-1 is described in this paper. The chiral part of the molecule was prepared by reduction of an optically active β-ketosulfoxide. The all-trans trienic part was stereoselectively synthesized via reductive elimination of a 1,6-dibenzoate-2,4-diene with sodium amalgam.
- Solladie, Guy,Somny, Frederic,Colobert, Francoise
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p. 801 - 810
(2007/10/03)
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- Synthesis of Optically Active α-Alkylidene-β-hydroxy-γ-methylenebutyrolactones. Isoobtusilactones and Isomahubalactones (Isomahubanolide and Isomahubenolide)
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The title compounds were prepared via stereoselective aldol reaction of α,β-unsaturated carboxylate α-anion equivalent, derived from optically active α-(arylsulfinyl)carboxylate and bromomagnesium diisopropylamide, with propargyl aldehyde as a key step.
- Nokami, Junzo,Ohtsuki, Hirotoshi,Sakamoto, Yasuhuko,Mitsuoka, Masayuki,Kunieda, Norio
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p. 1647 - 1650
(2007/10/02)
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- O-sulfinylation with methanesulfonyl cyanide or p-toluenesulfonyl cyanide and DBU
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Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates is suggested.
- Barton,Jaszberenyi,Theodorakis
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p. 2585 - 2588
(2007/10/02)
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- O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide
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Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]under-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.
- Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.
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p. 9167 - 9178
(2007/10/02)
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- Improved Preparation of Optically Active Methyl p-Tolyl Sulfoxide
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An improved large scale procedure for the preparation of optically pure methyl p-tolyl sulfoxide is described as well as a large scale preparation of optically pure (-) menthyl (S)-p-tolylsulfinate
- Solladie, Guy,Hutt, Jean,Girardin, Andre
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- The reactions of some α-halo-β-ketosulfones with hard and soft nucleophiles. A preparation of sulfinate esters
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The α-halo-β-ketosulfonyl functionality was attacked by ethanethiolate at the halogen which, in the presence of a proton source, usually resulted in reduction to the β-ketosulfone.A range of other soft nucleophiles did not react, whereas hard nucleophiles invariably attacked at the carbonyl, with subsequent cleavage to α-halosulfones.Ambident arylsulfinate anions usually attacked at halogen to form the sulfonyl halide, which reacted with excess sulfinate to give an intermediate that is readily attacked by alcohols.This reaction resulted in the formation of alkyl arylsulfinate esters in reasonable yields.The same reaction occurred when sulfonyl chlorides were reacted with sulfinate salts and it was rationalized by using HSAB principles.Spectral properties of some sulfinate esters are presented.
- Grossert, J. Stuart,Dubey, Pramod K.,Elwood, Tom
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p. 1263 - 1267
(2007/10/02)
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- Microbial Oxidation of Alkyl Aryl Sulfides to the Corresponding Optically Active Sulfoxides
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Incubation of alkyl aryl sulfides with growing cells of Corynebacterium equi IFO 3730 afforded the corresponding sulfoxides and sulfones.The selectivity for the formation of sulfoxides over sulfones was higher with sulfides which have shorter alkyl chains.When methyl sulfides were used as substrates, formation of the corresponding sulfones was completely suppressed.Sulfoxides were revealed to have 87-100percent optically purities as to the (R) absolute configuration by HPLC analysis.The culture conditions seriously influenced the yield of oxidation products.High conversion of sulfides was attained when the reaction was carried out with grow ing cells in the logarithmic phase, in medium containing hexadecane as the carbon and energy source.
- Ohta, Hiromichi,Okamoto, Yasushi,Tsuchihashi, Gen-ichi
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p. 671 - 676
(2007/10/02)
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- SYNTHESIS OF POTENTIALLY ALLERGENIC CHIRAL α-(HYDROXYALKYL)ACRYLATES
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The title componds have been synthesized with 75percent enantiomeric excess from chiral p-tolylsulfoxides 1 and aldehydes, followed by thermal elimination of the sulfoxide.
- Papageorgiou, Christos,Benezra, Claude
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p. 1303 - 1306
(2007/10/02)
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- Novel One-Step Preparation of Sulfinic Acid Derivatives from Sulfinic Acid
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Convenient one-step syntheses of sulfinamides and sulfinate esters from sulfinic acids were achieved by using coupling reagents, such as 2-chloro-1-methylpyridinium iodide, γ-saccharine chloride, N,N'-dicyclohexylcarbodiimide, and diethyl azodicarboxylate and triphenylphosphine.Ammonolysis of sulfinate esters also give sulfinamides.Keyword- sulfinic acid; sulfinamide; sulfinate ester; sulfinyl-transfer reagent; coupling reaction; 2-chloro-1-methylpyridinium iodide; γ-saccharine chloride; N,N'-dicyclohexylcarbodiimide; diethyl azodicarboxylate; triphenylphosphine
- Furukawa, Mitsuru,Ohkawara, Tadashi,Noguchi, Yoshihide,Nishikawa, Masumi,Tomimatsu, Masahide
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p. 134 - 141
(2007/10/02)
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- SYNTHESE ET PROPRIETES D'UN TENSIOACTIF CATIONIQUE CHIRAL D'UN TYPE NOUVEAU, PORTEUR DE LA CHARGE SUR LE CENTRE ASYMETRIQUE
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Surfactants in which the charge-bearing atom is chiral show catalytic properties in micellar solutions similar to those of corresponding quaternary ammonium salts.No stereoselectivity was observed in the catalytic reactions.It is clear therefore that pres
- Juge, S.,Meyer, G.
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p. 959 - 964
(2007/10/02)
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- SYNTHESES ASYMETRIQUES DE β-HYDROXYACIDES PAR CONDENSATION D'ANIONS ENOLATES D'ESTERS α-SULFINYLE CHIRAUX SUR DES COMPOSES CARBONYLES
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A stereospecific synthesis of (R)-(+)-t-butyl p-tolylsulfinyl acetate 2 is described.The aldol-type condensation of this reagent leads to β-hydroxyacids in good chemical and optical yields.The determination of the absolute configuration of the condensatio
- Mioskowski, Charles,Solladie, Guy
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p. 227 - 236
(2007/10/02)
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