- Ynamides as Three-Atom Components in Cycloadditions: An Unexplored Chemical Reaction Space
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While 1,3-dipolar cycloadditions have appeared to be a fertile area for research, as attested by the numerous synthetic transformations and resulting applications that have been developed during the past 60 years, the use of neutral three-Atom components (TACs) in (3+2) cycloadditions remains comparatively sparse. Neutral TACs, however, have great synthetic potential given that their reaction with a πsystem can produce zwitterionic cycloadducts that may be manipulated for further chemistry. We report herein that ynamides, a class of carbon πsystems that has seen wide interest over the last two decades, can be used as neutral TACs in thermally induced intramolecular (3+2) cycloaddition reactions with alkynes to yield a variety of functionalized pyrroles. The transformation is proposed to occur in a stepwise manner via the intermediacy of a pyrrolium ylide, from which the electron-withdrawing group on the nitrogen atom undergoes an intramolecular 1,2-shift to produce the neutral pyrrole. This work demonstrates a yet unexplored facet of ynamide reactivity with great potential in heterocyclic chemistry.
- Campeau, Dominic,Gagosz, Fabien,Pommainville, Alice
-
supporting information
p. 9601 - 9611
(2021/07/19)
-
- Silver-Catalyzed Annulation of Arynes with Nitriles for Synthesis of Structurally Diverse Quinazolines
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An efficient silver catalyzed annulation reaction of aryne with nitriles to generate quinazolines is described. Arynes generated from triynes or tetraynes through a hexadehydro Diels-Alder reaction readily participated in an [A + 2B] mode of annulation with nitriles in the presence of AgSbF6 catalyst. The mechanism was explored by DFT calculations, which supports the silver-catalyzed formation of nitrilium ion as a key intermediate. This annulation generates an array of polysubstituted novel quinazoline derivatives with excellent regioselectivity.
- Ghorai, Sourav,Lin, Yongjia,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung
-
supporting information
p. 626 - 630
(2020/01/31)
-
- Silver-Catalyzed Selective Multicomponent Coupling Reactions of Arynes with Nitriles and Isonitriles
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Pathway selective aryne-based novel multicomponent coupling reactions with isonitriles and nitriles are described. Crucial to these reactions is the formation of a silver-aryne complex, which shows differential reactivity toward isonitriles and nitriles to form two different forms of ortho-nitrilium organosilver arene species. Interception of the nitrilium of an aryne-isonitrile adduct with another isonitrile leads to the formation of benzocyclobutene-1,2-diimines, whereas the nitrilium of an aryne-nitrile adduct renders selective formation of 3H-indol-3-imines or 3-iminoindolin-2-ol depending on the structure of the nitrile employed.
- Ghorai, Sourav,Lin, Yongjia,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung
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supporting information
p. 642 - 647
(2020/01/31)
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- Cationic Amphiphiles Bearing a Diacetylenic Function in the Headgroup: Aggregative Properties and Polymerization
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In the wide panorama of diacetylenic lipids, the photoresponsive conjugated 1,3-diyne function is usually encased into the hydrocarbon chain of the amphiphile at a variable distance from the headgroup. Therefore, the polydiacetylene network obtained by polymerization upon UV irradiation of the corresponding liposomes, exploited as sensing function, is embedded in the hydrophobic region of liposomes. Structurally related cationic diacetylenic amphiphiles featuring the conjugated triple bonds proximate to charged nitrogen were synthesized and evaluated in their ability to polymerize under aggregative conditions. The occurrence of polymerization only in certain aggregating conditions was rationalized by nuclear magnetic resonance (NMR) and Langmuir trough experiments.
- Mauceri, Alessandro,Giansanti, Luisa,Capitani, Donatella,Sobolev, Anatoly,Galantini, Luciano,Bassetti, Mauro,Nemi, Maria Grazia,Gradella Villalva, Denise,Battista, Sara,Mancini, Giovanna
-
p. 12168 - 12178
(2020/12/01)
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- BROMINATED FLAME RETARDANTS AND POLYURETHANES CONTAINING THE SAME
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The disclosure includes brominated alkenyl alcohols, their use as a flame retardant in polyurethane and polyurethane foams, and polyurethanes containing the brominated alkenyl alcohols. Compositions, methods, and processes are disclosed. The brominated alkenyl alcohols used as flame retardants in polyurethanes can be generally described by Formula (I), the scope of which is disclosed herein.
- -
-
Paragraph 0128; 0129
(2020/07/15)
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- Synthesis of Imides, Imidates, Amidines, and Amides by Intercepting the Aryne-Isocyanide Adduct with Weak Nucleophiles
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New aryne-based multicomponent coupling reactions for the formation of functionalized aromatic compounds have been developed. Arynes generated from triynes or tetraynes through the hexadehydro Diels-Alder reaction readily react with isocyanide to generate nitrilium intermediate. Intercepting this nitrilium species with various weak nucleophile including carboxylic acids, alcohols, sulfonamides, or water generated the corresponding imides, imidates, amidines, or amides. The high regioselectivity of these transformations was mainly controlled by the substituents of the arynes.
- Ghorai, Sourav,Lee, Daesung
-
supporting information
p. 7390 - 7393
(2019/10/02)
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- Highly Selective Manganese(I)/Lewis Acid Cocatalyzed Direct C?H Propargylation Using Bromoallenes
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A manganese(I)/Lewis acid cocatalyzed direct C?H propargylation with high selectivity has been developed. BPh3 was discovered to not only promote the reactivity, but also enhance the selectivity. Secondary, tertiary, and even quaternary carbon centers at the propargylic position could be directly constructed. Both internal and terminal alkynes are easily accessible. The chirality was successfully transferred from an axially chiral allene to central chirality. The reactivity of the manganese catalyst in this reaction was found to be unique among transition metal catalysts.
- Zhu, Can,Schwarz, Jonas Luca,Cembellín, Sara,Gre?ies, Steffen,Glorius, Frank
-
supporting information
p. 437 - 441
(2018/02/21)
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- Synthesis and evaluation of colletoic acid core derivatives
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Cortisol homeostasis has been linked to the pathogenesis of metabolic syndrome (MetS), since it stimulates hepatic gluconeogenesis and adipogenesis. MetS is classified as a constellation of health conditions that increase the risk of type 2 diabetes and cardiovascular disease. Intracellular cortisol levels are regulated by 11β-hydroxysteroid dehydrogenase (type 1 and type 2) in a tissue dependent manner. The type 1 enzyme (11β-HSD1) is widely expressed in glucocorticoid targeted tissues and is responsible for the conversion of cortisone to the active cortisol. Local reduction of cortisol regeneration presents a potential strategy for MetS treatment. Recently we disclosed the total synthesis of (+)-colletoic acid as a potent 11β-HSD1 inhibitor. Herein, we describe our improved processing chemistry for the synthesis of the colletoic acid core to access a diverse number of derivatives for evaluation against 11β-HSD1. The Evan's chiral auxiliary was utilized to construct the acyclic precursor 12 to afford the acorane core 9 using a modified Heck reaction in excellent chemical yields. The colletoic acid core derivatives showed modest activity against 11β-HSD1 and will serve for further biological evaluation.
- Ling, Taotao,Gautam, Lekh Nath,Griffith, Elizabeth,Das, Sourav,Lang, Walter,Shadrick, William R.,Shelat, Anang,Lee, Richard,Rivas, Fatima
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supporting information
p. 126 - 132
(2016/02/05)
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- Ravynic acid, an antibiotic polyeneyne tetramic acid from: Penicillium sp. elucidated through synthesis
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A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 g mL-1.
- Myrtle,Beekman,Barrow
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p. 8253 - 8260
(2016/09/09)
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- Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles
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The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.
- Karmakar, Rajdip,Yun, Sang Young,Chen, Jiajia,Xia, Yuanzhi,Lee, Daesung
-
supporting information
p. 6582 - 6586
(2015/06/02)
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- Silver-catalysed intramolecular hydroamination of alkynes with trichloroacetimidates
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Silver(i) complexes catalyse the intramolecular addition of trichloroacetimidates to alkynes. In the absence of a ligand, the selectivity of the reaction is dependent upon the nature of the counter-anion and solvent. The introduction of non-chelating nitrogeneous ligands suppresses competitive Bronsted acid catalysis, improving the yield and selectivity of the reaction.
- Wong, Valerie H. L.,Hor, T. S. Andy,Hii, King Kuok
-
supporting information
p. 9272 - 9274
(2013/10/01)
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- Stereocontrolled synthesis of a Cn-Cn+7 building block ("eastern moiety") for the unnatural enantiomers of important polyol,polyene antibiotics based on a ring-closing metathesis and an aldol addition of a lactone enolate
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A stereocontrolled synthesis of epoxide 6, which represents the C n-Cn+7 or "eastern moiety" building block for the title compounds, has been realized in 19 steps. Our synthesis started from tetrabromoacetone 26 and afforded dibromotriene 33b in six steps. The latter was subjected to a ring-closing metathesis, which gave the dibromovinyl-substituted lactone 34 in high yield. A highly stereoselective conjugate addition/enolate aldolization sequence established the additional stereocenters with perfect selectivity. Epoxide 47b was reached in another eight steps, which included a C-SiMe2Pha€‰→a€‰C-OH oxidation in the presence of an acetal group. The final structure 6 was completed by hydrostannylation/brominolysis. A dibromovinyl-substituted unsaturated δ-lactone obtained by ring-closing metathesis underwent a highly diastereoselective silyl cuprate 1,4-addition/aldolization sequence. Tamao-Fleming oxidation transformed the silyl into a hydroxy group. Alkyne formation, hydrostannylation, and N-bromosuccinimidolysis converted the dibromovinyl into a trans-bromovinyl moiety. Copyright
- Kamptmann, Sonja B.,Brueckner, Reinhard
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p. 6584 - 6600
(2013/11/06)
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- Reactivity pattern of bis(propargyloxy) disulfides: Tandem rearrangements and cyclizations
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Thirty-five substituted bis(propargyloxy) disulfides were successfully prepared in good to excellent yields, and their reactivity was found to be strongly dependent on the substitution pattern of the reactant. Inter alia they undergo surprising tandem sigmatropic rearrangements and cycloadditions. Three heretofore unknown product types were isolated and fully characterized: 6,7-dithiabicyclo[3.1.1]heptan-2-one 6-oxide derivatives, two isomeric 1,2-dithiete 1,1-dioxides (α,β-unsaturated four-membered cyclic thiosulfonates) from bis(propargyloxy) disulfides with α- or γ-alkyl-substituted propargyl groups, and two isomeric 2-oxa-5,7-dithiabicyclo[2.2.1]heptane 5-oxides from bis(propargyloxy) disulfides with α-tert-butyl- or α,α-dialkyl-substituted propargyl groups. Georg Thieme Verlag Stuttgart - New York.
- Braverman, Samuel,Pechenick-Azizi, Tatiana,Gottlieb, Hugo E.,Sprecher, Milon
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experimental part
p. 1741 - 1750
(2011/07/09)
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- From highly enantioselective catalytic reaction of 1,3-diynes with aldehydes to facile asymmetric synthesis of polycyclic compounds
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(S)-1,1′-Binaphth-2-ol (BINOL) in combination with ZnEt2, Ti(OiPr)4, and biscyclohexylamine was found to catalyze the highly enantioselective (83-95% ee) addition of various 1,3-diynes to aldehydes of diverse structures. This method provides a convenient pathway to generate a number of optically active dienediynes as the acyclic precursors to polycyclic compounds. The chiral dienediynes undergo highly chemoselective Pauson-Khand (PK) cycloaddition in benzaldehyde by using [Rh(cod)Cl]2 as the catalyst in the presence of rac-BINAP. High diastereoselectivity (up to >20:1) has also been achieved with the chiral dienediyne substrates containing a bulky substituent adjacent to the chiral center. In the presence of the Grubbs II catalyst, ring-closing enyne metathesis of the PK cycloaddition products led to the formation of the desired 5,5,7- and 5,5,8-fused tricyclic compounds. Further highly diastereoselective Diels-Alder reaction of a 5,5,7-tricyclic compound with maleic anhydride produced a 5,5,7,6-polycyclic product. The asymmetric synthesis of polycyclic compounds from optically active dienediynes has established a novel and efficient synthetic route to the structural framework of many biologically significant molecules.
- Turlington, Mark,Du, Yuhao,Ostrum, Samuel G.,Santosh, Vishaka,Wren, Kathryne,Lin, Tony,Sabat, Michal,Pu, Lin
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supporting information; scheme or table
p. 11780 - 11794
(2011/09/16)
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- Synthesis of simple diynals, diynones, their hydrazones, and diazo compounds: Precursors to a family of dialkynyl carbenes (R1-C-C- C-C-C-R2)
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A variety of substituted pentadiynols, -diynals, and -diynones have been prepared en route to precursors to dialkynyl carbenes (R1-C-C-C- C-C-R2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4 + 1, 3 + 2, 2 + 2 + 1, and 2 + 1 + 1 + 1 coupling methodologies. The Dess-Martin periodinane serves as an excellent method for the oxidation of pentadiynols to diynals and diynones, although many of the oxidized products are sufficiently reactive that they were not isolated; rather, they were generated in situ and intercepted with nucleophiles such as tosylhydrazide or trisylhydrazide. The hydrazone derivatives are generally reliable precursors to diazo compounds and carbenes, although cyclization of the hydrazone to afford a pyrazole can be a complicating factor in certain instances.
- Bowling, Nathan P.,Burrmann, Nicola J.,Halter, Robert J.,Hodges, Jonathan A.,McMahon, Robert J.
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experimental part
p. 6382 - 6390
(2010/12/19)
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- THERAPEUTIC COMPOUNDS
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The invention relates to novel resolvin compounds and pharmaceutical preparations thereof. The invention further relates to methods of treatment using the novel resolvin compounds of the invention.
- -
-
Page/Page column 106
(2010/04/27)
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- COMPOSITIONS AND METHODS FOR ORGAN PRESERVATION
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The invention relates to reducing, preventing or reversing organ damage, reducing and/or preventing stem cell damage and/or death, enhancing organ preservation and/or survival, or enhancing stem cell preservation and/or survival comprising administering a compound of formula A, a compound of any one of formulae 1-49 or 1-111, a lipoxin compound, an oxylipin compound, or a combination of aspirin and an omega-3 fatty acid.
- -
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Page/Page column 113
(2010/08/18)
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- Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B and an analogue
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The asymmetric synthesis of the marine sponge natural products R-strongylodiols A R-1 and B R-2, using a minimum protection strategy, is described. Two approaches were examined and the Noyori asymmetric reduction of ynones was found to be successful for installing the chirality of the natural products. Analogue R-32 was also prepared. In addition, asymmetric alkynylation of aldehydes is briefly reviewed.
- Kirkham, James E.D.,Courtney, Timothy D.L.,Lee, Victor,Baldwin, Jack E.
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p. 7219 - 7232
(2007/10/03)
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- The geometric isomers of methyl-2,4,6-decatrienoate, including pheromones of at least two species of stink bugs
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All eight geometric isomers of methyl 2,4,6-decatrienoate were synthesized from readily accessible starting materials by fully exploiting Wittig-type olefinations, and taking advantage of an easy separation of 2E and 2Z unsaturated esters. The aggregation pheromone of the brown-winged green bug, Plautia stali, methyl (E,E,Z)-2,4,6-decatrienoate (also a cross-attractant for the brown marmorated stink bug, Halyomorpha halys), was expediently produced in two easy steps from (E)-4,4-dimethoxy-2-butenal in 55% yield. The sex pheromone of the red-shouldered stink bug, Thyanta pallidovirens, methyl (E,Z,Z)-2,4,6-decatrienoate, was conveniently synthesized from 2,4-octadiyn-1-ol in 32% yield using in situ manganese dioxide oxidation-Wittig condensation in a key step.
- Khrimian, Ashot
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p. 3651 - 3657
(2007/10/03)
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- Single-crystal-to-single-crystal topochemical polymerizations of a terminal diacetylene: Two remarkable transformations give the same conjugated polymer
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Host-guest chemistry was used to prepare a cocrystal of a dipyridyl substituted oxalamide host and a resorcinol derivative of a terminal diacetylene. X-ray crystallography revealed that the molecules assemble into a triple-helix with the diacetylene functionalities aligned in the center of the helix. Upon heating, the diacetylenes polymerize to give the corresponding polymer. In a second experiment, the X-ray structure of the crystalline hydrate of the same diacetylene also showed a suitable alignment of the diacetylene functionalities. These crystals polymerize at only 50 °C with the C1 carbon end of the diacetylene undergoing an unprecedented 2.4 A inward swinging movement. This results in a remarkable 9% increase in crystal density. These are the first structurally characterized polymerizations of any terminal diacetylene. A detailed comparison of the two sets of structural changes offers an interesting insight into the precise trajectories of polymerization reactions. Copyright
- Ouyang, Xi,Fowler, Frank W.,Lauher, Joseph W.
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p. 12400 - 12401
(2007/10/03)
-
- Asymmetric synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid
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A short and efficient enantio selective synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid was successfully developed. Trifluoromethylation of benzyl-protected bromoalkene 4 provided key intermediate trifluoromethylated transdi-substituted alkene 2 in good yield. The sequence then involved Sharpless asymmetric dihydroxylation, nucleophilic opening of cyclic sulfate with NaN3, palladium-catalyzed selective hydrogenation, and oxidation.
- Jiang, Zhong-Xing,Qin, Ying-Ying,Qing, Feng-Ling
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p. 7544 - 7547
(2007/10/03)
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- Bulky trialkylsilyl acetylenes in the Cadiot-Chodkiewicz cross-coupling reaction
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Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and tri-isopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio- and stereoselectively into enynes by hydrotelluration, carbometalation, and reduction reactions.
- Marino, Joseph P.,Nguyen, Hanh Nho
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p. 6841 - 6844
(2007/10/03)
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- Synthesis and cytotoxic activity of a series of diacetylenic compounds related to falcarindiol
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The synthesis of a series of diacetylenic compounds related to the natural product falcarindiol has been carried out. Unsymmetrical diacetylenes were prepared by a modification of the Cadiot-Chodkiewicz coupling reaction, while a Glaser coupling was used to prepare symmetrical diacetylenes. These compounds have been tested for in vitro cytotoxic activity against Hep-G2, and H-4-II-E cell lines. Diacetylenes with additional unsaturation at C-1, 2, appended with hydroxyl groups at C-3 and C-8, or with long hydrophobic chains, exhibited IC50 values in the micromolar range.
- Setzer,Gu,Wells,Setzer,Moriarity
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p. 1776 - 1777
(2007/10/03)
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- Glycosidase inhibitors: Synthesis of enantiomerically pure aza-sugars from Schiff base amino esters via tandem reduction-alkenylation and osmylation
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Nitrogen-in-the-ring 'aza-sugars' have been synthesized in enantiomerically pure form from the amino acid L-alanine in excellent overall yield. The O'Donnell's Schiff base of L-alanine methyl ester 9a was converted to aza-sugar L-fuco-1-deoxy-nojirimycin, 18, and to the epimer L-gulo-1- deoxy-nojirimycin, 20, in eight steps. The overall yields were 20 and 29%, respectively. The methodology for the efficient generation of silyl- and benzyl-protected (E)-3-lithio-2-propen-1-ols, and the use of these alkenyllithiums with iBu5Al2H as nucleophiles in the threo-selective tandem reduction-alkenylation of the Schiff base esters is described. Osmium- catalyzed cis-oxygenation of the resulting olefin products was selective for the galacto (fuco) amino polyols in all cases for the acyclic olefins, and was gulo-selective for the cyclic D-4,5-dihydropyridine pivalate, 17c. TEMPO- NaOCl was selective for oxidation of the primary position of the acyclic Schiff bases, and allowed for minimal protection/deprotection of the intermediates. The resulting N-benzhydryl heterocycles were easily deprotected with H2-Pd at atmospheric pressure.
- Polt, Robin,Sames, Dalibor,Chruma, Jason
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p. 6147 - 6158
(2007/10/03)
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- The polymer-supported Cadiot-Chodkiewicz coupling of acetylenes to produce unsymmetrical diynes
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Cu(II)-catalyzed coupling of polymer-bound' ω-haloalkyn-1-ols to terminal alkynes proceeds in moderate yield to give unsymmetrical diynes upon hydrolytic removal from the polymer. Formation of the symmetrical homocoupled byproduct is suppressed relative to conventional Cadiot-Chodkiewicz conditions in homogeneous solution.
- Montierth, John M.,DeMario, Dierdre R.,Kurth, Mark J.,Schore, Neil E.
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p. 11741 - 11748
(2007/10/03)
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- Synthesis, vapor growth, polymerization, and characterization of thin films of novel diacetylene derivatives of pyrrole. The use of computer modeling to predict chemical and optical properties of these diacetylenes and poly(diacetylenes)
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In the present work two diacetylene derivatives of pyrrole (compounds 1 and 2), which are predicted by semiempirical AMI calculations to have very different properties, are synthesized; the polymerizability of these diacetylenes in the solid state is determined; and the results are compared to the computer predictions. Diacetylene 1 is novel in that the monomer is a liquid at room temperature; this may allow for the possibility of polymerization in the liquid state as well as the solid state. Thin poly(diacetylene) films are obtained from compound 1 by growing films of the monomer using vapor deposition and polymerizing with UV light; these films are then characterized. Interestingly, while the poly(diacetylene) from 1 does not possess good nonlinear optical properties, the monomer exhibits very good third-order nonlinear optical effects (e.g., phase conjugation) in solution. Dilute acetone solutions of the monomer 1 give intensity-dependent refractive indices (η2) on the order of 10-6 esu (x(3) values on the order of 10-7 esu); these are 106 times better than for CS2.
- Paley,Frazier,Abeledeyem,McManus,Zutaut
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p. 3247 - 3251
(2007/10/02)
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- Halogenation of alkynes and alkynylsilanes
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Halogenation of alkynes has given 1,2-dihalogenoalkenes in good yields.Bromination of alkynylsilanes has given 1,2-dibromovinylsilanes, and reactions with iodine chloride mainly iodoalkynes.
- Al-Hassan, Mohammed I.
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p. 183 - 186
(2007/10/02)
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- SUBSTITUTION DES HALOGENO-1 ALCYNES-1 PAR LES DERIVES ORGANOMETALLIQUES DU CUIVRE. ACCES A UNE NOUVELLE CLASSE DE SYNTHONS: APPLICATION A LA SYNTHESE DU BOMBYKOL
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1-Bromo- and 1-iodo-1-alkynes are alkylated by organocopper(I) compounds.Alkenylcopper(I) derivatives undergo substitution with retention of configuration leading to conjugated and functional enynes, from which conjugated dienes can be obtained.
- Commercon, A.,Normant, J. F.,Villieras, J.
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p. 1215 - 1222
(2007/10/02)
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