- Synthesis of novel functionalized N-tosylaldimines
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Condensation of a variety of aromatic aldehydes with p-toluenesulfonamide in the presence of Lewis acids affords novel functionally varied aromatic N-tosylaldimines in good yields. A diverse array of aromatic aldehydes was examined, each containing a uniq
- Wynne, James H.,Price, Stacy E.,Rorer, Jeffrey R.,Stalick, Wayne M.
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- Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange
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Lithium-iodine exchange on alkyl- or aryl-substituted N-tosyliodoaziridines afforded unstabilized aziridinyllithiums, which were subsequently trapped at low temperatures with a range of carbon and heteroatom electrophiles affording cis-substituted aziridi
- Boultwood, Tom,Bull, James A.
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- Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor
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B2Pin2-assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol a
- He, Yi,Li, Shi-Guang,Mbaezue, Ifenna I.,Reddy, Angula C.S.,Tsantrizos, Youla S.
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supporting information
(2021/03/24)
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- Synthesis and biological evaluation of substituted phenyl azetidine-2-one sulphonyl derivatives as potential antimicrobial and antiviral agents
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In the present study, we intend to synthesize a series of novel substituted phenyl azetidine-2-one sulphonyl derivatives. The entire set of derivatives 5 (a-t) were screened for in-vitro antibacterial, and antifungal activity, and among them eleven compou
- Mandal, Milan Kumar,Ghosh, Swagatika,Bhat, Hans Raj,Naesens, Lieve,Singh, Udaya Pratap
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- Asymmetric Catalysis in Liquid Confinement: Probing the Performance of Novel Chiral Rhodium–Diene Complexes in Microemulsions and Conventional Solvents
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The role of liquid confinement on the asymmetric Rh catalysis was studied using the 1,2-addition of phenylboroxine (2) to N-tosylimine 1 in the presence of [RhCl(C2H4)2]2 and chiral diene ligands as benchmark reaction. To get access to Rh complexes of different polarity, enantiomerically pure C2-symmetric p-substituted 3,6-diphenylbicyclo[3.3.0]octadienes 4 and diastereomerically enriched unsymmetric norbornadienes 5 and 6 carrying either the Evans or the SuperQuat auxiliary were synthesized. A microemulsion containing the equal amounts of H2O/KOH and toluene/reactants was formulated using the hydrophilic sugar surfactant n-octyl β-d-glucopyranoside (C8G1) to mediate the miscibility between the nonpolar reactants and KOH, needed to activate the Rh–diene complex. Prominent features of this organized reaction medium are its temperature insensitivity as well as the presence of water and toluene-rich compartments with a domain size of 55 ? confirmed by small-angle X-ray scattering (SAXS). Although bicyclooctadiene ligands 4 a,b,e performed equally well under homogeneous and microemulsion conditions, ligands 4 c,d gave a different chemoselectivity. For norbornadienes 5, 6, however, microemulsions markedly improved conversion and enantioselectivity as well as reaction rate, as was confirmed by kinetic studies using ligand 5 b.
- Deimling, Max,Kirchhof, Manuel,Schwager, Barbara,Qawasmi, Yaseen,Savin, Alex,Mühlh?user, Tina,Frey, Wolfgang,Claasen, Birgit,Baro, Angelika,Sottmann, Thomas,Laschat, Sabine
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supporting information
p. 9464 - 9476
(2019/07/04)
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- Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines
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Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.
- Schrapel, Carmen,Frey, Wolfgang,Garnier, Delphine,Peters, René
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supporting information
p. 2448 - 2460
(2017/02/23)
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- Exogenous-Base-Free Palladacycle-Catalyzed Highly Enantioselective Arylation of Imines with Arylboroxines
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Enantiomerically pure benzylic amines are important for the development of new drugs. A readily accessible planar-chiral ferrocene-derived palladacycle is shown to be a highly efficient catalyst for the formation of N-substituted benzylic stereocenters; t
- Schrapel, Carmen,Peters, Ren
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supporting information
p. 10289 - 10293
(2015/09/01)
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- Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation
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(2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson-Corey-Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.
- Duan, Yaya,Zhou, Bin,Lin, Jin-Hong,Xiao, Ji-Chang
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supporting information
p. 13127 - 13130
(2015/08/18)
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- Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: Reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography
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The preparation of C-iodo-N-Ts-aziridines with excellent cis-diastereoselectivity has been achieved in high yields by the addition of diiodomethyllithium to N-tosylimines and N-tosylimine-HSO2Tol adducts. This addition-cyclization protocol succ
- Boultwood, Tom,Affron, Dominic P.,Trowbridge, Aaron D.,Bull, James A.
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p. 6632 - 6647
(2013/07/26)
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- Solvent-free synthesis of N-sulfonyl imines using WCl6 as a novel, highly efficient and reusable catalyst
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WCl6 was used as a novel, efficient and reusable catalyst for the preparation of N-sulfonyl imines via the condensation of sulfonamides with aldehydes as well as isatin under solvent-free conditions. The turn-over frequency (TOF) value of the c
- Zolfigol, Mohammad Ali,Tavasoli, Mahsa,Moosavi-Zare, Ahmad Reza,Arghavani-Hadi, Parastoo,Zare, Abdolkarim,Khakyzadeh, Vahid
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p. 7692 - 7696
(2013/07/05)
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- Asymmetric cyanation of a-ketiminophosphonates catalyzed by cinchona alkaloids: Enantioselective synthesis of tetrasubstituted a-aminophosphonic acid derivatives from trisubstituted a-aminophosphonates
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An enantioselective synthesis of tetrasubstituted a-phosphono-a-amino nitriles through asymmetric cyanation of a-ketiminophosphonates catalyzed by Cinchona alkaloids is reported. a-Ket- ACHTUNGTRENUNGiminophosphonates are generated, in a very efficient sy
- Vicario, Javier,Ezpeleta, Jose Mari,Palacios, Francisco
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supporting information
p. 2641 - 2647
(2013/01/15)
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- Efficient and convenient preparation of N-tosylimines catalyzed by indium trichloride
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A new method for preparation of N-tosylimines by InCl3-mediated condensation of aldehydes with p-toluenesulfonamide in refluxing benzene is reported. The procedure is lauded by its simplicity, mild reaction conditions, excellent yields and adap
- Deng, Gui Sheng,Zou, Jing Yuan,Sun, Teng Fei
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scheme or table
p. 511 - 514
(2012/01/05)
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- Cyanuric chloride-catalyzed synthesis of N-sulfonyl imines
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Cyanuric chloride is an inexpensive, efficient, and mild catalyst for the synthesis of N-sulfonyl imines by the reaction of sulfonamides with aryl aldehydes at 110°C under solvent-free conditions. This method affords the N-sulfonyl imines in short reactio
- Wu, Liqiang,Yang, Xiaojuan,Wang, Xiao,Yan, Fulin
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experimental part
p. 509 - 513
(2011/08/07)
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- Green, Catalyst-Free Protocol for the Efficient Synthesis of N-Sulfonyl Aldimines and Ketimines in Ionic Liquid [Bmim]Br
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Sulfonamides are efficiently condensed with aldehydes as well as ketones in the absence of catalyst in 1-butyl-3-methylimidazolium bromide ([bmim]Br) under microwave irradiation to afford N-sulfonyl aldimines and ketimines in good to excellent yields in s
- Zare, Abdolkarim,Moosavi-Zare, Ahmad Reza,Hasaninejad, Alireza,Parhami, Abolfath,Khalafi-Nezhad, Ali,Beyzavi, Mohammad Hassan
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experimental part
p. 3156 - 3165
(2009/11/30)
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- Triarylmethyl chlorides as novel, efficient, and mild organic catalysts for the synthesis of N-sulfonyl imines under neutral conditions
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A highly efficient procedure for the preparation of N-sulfonyl imines via condensation of sulfonamides with aldehydes as well as ketones in the presence of triarylmethyl chlorides as metal-free organo-catalysts at 40 °C is described. The advantages of thi
- Khalafi-Nezhad, Ali,Parhami, Abolfath,Zare, Abdolkarim,Shirazi, Amir Nasrolahi,Zare, Ahmad Reza Moosavi,Hassanimejad, Alireza
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p. 456 - 461
(2008/09/20)
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- A facile synthesis of N-sulfonyl and N-sulfinyl aldimines under Barbier-type conditions
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(Chemical Equation Presented) A convenient synthesis of N-sulfonyl- and N-sulfinylimines by the condensation of aldehydes with sulfonyl or sulfinyl amides in the presence of benzyl bromide and zinc dust at room temperature under the Barbier-type condition
- Fan, Renhua,Pu, Dongming,Wen, Fengqi,Ye, Yang,Wang, Xiaoli
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p. 3623 - 3625
(2008/09/20)
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- One-step synthesis of substituted dihydro- and tetrahydroisoquinolines by FeCl3·6H2O catalyzed intramolecular Friedel-Crafts reaction of benzylamino-substituted propargylic alcohols
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(Chemical Equation Presented) A mild, versatile, and efficient method for the one-step synthesis of substituted dihydro- and tetrahydroisoquinolines has been developed by the FeCl3·6H2O catalyzed intramolecular allenylation/cyclization reaction of benzylamino-substituted propargylic alcohols, representing the first example of the intramolecular Friedel-Crafts reaction of propargylic alcohols.
- Huang, Wen,Shen, Quansheng,Wang, Jialiang,Zhou, Xigeng
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p. 1586 - 1589
(2008/09/17)
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- Small-molecule inhibitors of protein geranylgeranyltransferase type I
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Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics. Copyright
- Castellano, Sabrina,Fiji, Hannah D. G.,Kinderman, Sape S.,Watanabe, Masaru,De Leon, Pablo,Tamanoi, Fuyuhiko,Kwon, Ohyun
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p. 5843 - 5845
(2008/03/14)
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- Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines
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Organocatalytic direct anti-selective Mannich reactions of O-TBS-hydroxyacetone with various N-tosylimines derived from aromatic aldehydes in the presence of L-threonine-derived catalyst afforded 1,2-amino alcohols in good yields and with enantioselectivi
- Cheng, Lili,Han, Xiao,Huang, Huiming,Wong, Ming Wah,Lu, Yixin
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p. 4143 - 4145
(2008/03/18)
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- Practical and general entry to N-tosyl aryl aldimines promoted by sulfamic acid in water and alcohol
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A practical, indirect procedure composed of a three-component condensation using aromatic aldehydes, p-tosylamide, and sodium p-toluenesulfinate in the presence of sulfamic acid in tap water-alcohol solvents to afford amidosulfones, and the subsequent wat
- Li, Zhenjiang,Ren, Xinhua,Shi, Yuhu,Ouyang, Pingkai
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p. 713 - 724
(2007/10/03)
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- An efficient and convenient procedure for preparation of N-sulfonylimines catalysed by TiO2/SO42- solid superacid
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A facile synthesis of N-sulfonylimines in good to excellent yields was described from aldehydes with sulfonamides catalysed by TiO2/SO 42- solid superacid.
- Jin, Tong-Shou,Feng, Guo-Liang,Yang, Mi-Na,Li, Tong-Shuang
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p. 591 - 593
(2007/10/03)
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- Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: Use of phenyldiazomethane, diazoesters and diazoacetamides
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Imine aziridination using diazo-compounds and catalytic quantities of metal salts and sulfides has been investigated. A range of imines derived from benzaldehyde bearing electron-withdrawing groups (N-Ts,N-SO2CH2CH2SiMesu
- Aggarwal,Ferrara,O'Brien,Thompson,Jones,Fieldhouse
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p. 1635 - 1643
(2007/10/03)
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- Asymmetric synthesis of β-amino acids through application of chiral sulfoxide
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This paper describes asymmetric synthesis of β-aminophenylpropionic acid through application of a homochiral sulfoxide auxiliary. High kinetically controlled (3R,2S,RS)-diastereoselectivity (-60°C) is achieved during addition of the lithium enolate of tert-butyl (+)-(R)-p-toluenesulfinylacetate to substituted N-(benzylidene)toluene-4-sulfonamides 2a-2d. The reductive cleavage of adduct 3a with sodium amalgam yielded tert-butyl 3-(toluene-4-sulfonamido)-3-phenylpropionate 5a, which was subjected to ester hydrolysis and subsequent detosylation with sodium in liquid ammonia to yield (S)-β-aminophenylpropionic acid in good yield and high 91% e.e.
- Sivakumar,Babu,Bhat, Sujata V.
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p. 1095 - 1099
(2007/10/03)
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