Asymmetric sulfa-Michael additions

被引:291
作者
Enders, Dieter [1 ]
Luettgen, Karsten [1 ]
Narine, Arun A. [1 ]
机构
[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源
SYNTHESIS-STUTTGART | 2007年 / 07期
关键词
sulfur compounds; asymmetric Michael additions; alpha; beta-unsaturated carbonyl compounds; tandem reactions; organocatalysis;
D O I
10.1055/s-2007-965968
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Numerous asymmetric methods have been developed over the past 30 years to effect the Michael reaction of sulfur donors and Michael acceptors. Many of these stoichiometric and catalytic methods are complementary to one another, each having a certain range of substrate tolerance. Organocatalysis has a place at the origin of this field in the discovery of cinchona alkaloid catalyzed sulfa-Michael reactions. At the same time, it is involved in the current state-of-the-art as several elegant tandem processes that employ secondary amine catalysts and involve initial sulfa-Michael additions have been developed.
引用
收藏
页码:959 / 980
页数:22
相关论文
共 115 条
[91]   HIGH-PRESSURE ASYMMETRIC MICHAEL ADDITIONS OF THIOLS, NITROMETHANE, AND METHYL OXOINDANCARBOXYLATE TO ENONES [J].
SERA, A ;
TAKAGI, K ;
KATAYAMA, H ;
YAMADA, H ;
MATSUMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1157-1161
[92]  
Seyden-Penne J., 2015, CHIRAL AUXILIARIES L, DOI [10.1002/(SICI)1099-0739(199705)11:5%3c457::AID-AOC568%3e3.0.CO
[93]  
2-L, DOI 10.1002/(SICI)1099-0739(199705)11:5%3C457::AID-AOC568%3E3.0.CO
[94]  
2-L]
[95]   Highly enantioselective synthesis of 1,3-mercapto alcohols from α,β-unsaturated ketones:: asymmetric bifunctional group exchange reaction [J].
Shiraki, H ;
Nishide, K ;
Node, M .
TETRAHEDRON LETTERS, 2000, 41 (18) :3437-3441
[96]  
Sibi MP, 2000, TETRAHEDRON, V56, P8033
[97]   Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks [J].
Skarzewski, J ;
Zielinska-Blajet, M ;
Turowska-Tyrk, I .
TETRAHEDRON-ASYMMETRY, 2001, 12 (13) :1923-1928
[98]   A new polymer-anchored chiral catalyst for asymmetric Michael addition reactions [J].
Sundararajan, G ;
Prabagaran, N .
ORGANIC LETTERS, 2001, 3 (03) :389-392
[99]   THE ENANTIOSELECTIVE MICHAEL ADDITION OF THIOLS TO CYCLOALKENONES BY USING (2S, 4S)-2-ANILINOMETHYL-1-ETHYL-4-HYDROXYPYRROLIDINE AS CHIRAL CATALYST [J].
SUZUKI, K ;
IKEGAWA, A ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (10) :3277-3282
[100]   ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE CYCLOHEXENOL DERIVATIVES VIA HIGHLY STEREOSELECTIVE REDUCTION OF (R)-3-(PARA-TERT-BUTYLPHENYLTHIO)CYCLOHEXAN-1-ONE [J].
SUZUKI, K ;
IKEGAWA, A ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1982, (06) :899-902