Enantioselective organocatalytic double Michael addition reactions

被引：143

作者：

Li, Hao ^{[1
]}

Zu, Liansuo ^{[1
]}

Xie, Hexin ^{[1
]}

Wang, Jian ^{[1
]}

Jiang, Wei ^{[1
]}

Wang, Wei ^{[1
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 09期

关键词：

D O I：

10.1021/ol070581y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel organocatalytic, enantioselective domino double Michael addition reaction of alpha,beta-unsaturated aldehydes with ethyl 4-mercapto-2-butenoate has been developed. The process is promoted by chiral diphenylprolinol TMS ether to give chiral tetrahydrothiophenes in high to excellent levels of enantioselectivities.

引用

页码：1833 / 1835

页数：3

共 63 条

[1] Enantioselective total synthesis of avrainvillamide and the stephacidins [J].

Baran, Phil S. ;

Hafensteiner, Benjamin D. ;

Ambhaikar, Narendra B. ;

Guerrero, Carlos A. ;

Gallagher, John D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8678-8693

[2] ENANTIOSELECTIVE SYNTHESIS OF (-)-MEROQUINENE THROUGH TANDEM MICHAEL REACTION METHODOLOGY [J].

BARCO, A ;

BENETTI, S ;

DERISI, C ;

POLLINI, GP ;

ROMAGNOLI, R ;

SPALLUTO, G ;

ZANIRATO, V .

TETRAHEDRON, 1994, 50 (08) :2583-2590

[3] Convenient 'one-pot' synthesis of 3,4-substituted tetrahydrothiophenes through tandem Michael-Henry and Michael-Michael reactions [J].

Barco, Achille ;

Baricordi, Nikla ;

Benetti, Simonetta ;

De Risi, Carmela ;

Pollini, Gian Piero .

TETRAHEDRON LETTERS, 2006, 47 (46) :8087-8090

[4]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[5] Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions [J].

Brandau, Sven ;

Maerten, Eddy ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14986-14991

[6] Direct amino acid catalyzed asymmetric synthesis of polyketide sugars [J].

Casas, J ;

Engqvist, M ;

Ibrahem, I ;

Kaynak, B ;

Córdova, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1343-1345

[7] Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids [J].

Chi, Yonggui ;

Gellman, Samuel H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6804-6805

[8] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[9] Biotin: A timeless challenge for total synthesis [J].

DeClercq, PJ .

CHEMICAL REVIEWS, 1997, 97 (06) :1755-1792

[10]

DEHMLOW EV, 1992, SYNTHESIS-STUTTGART, P947

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