Asymmetric conjugate addition of thiols to (E)-3-crotonoyloxazolidin-2-one by iron or cobalt/pybox catalyst

被引：60

作者：

Kawatsura, Motol ^{[1
]}

Komatsu, Yuji ^{[1
]}

Yamamoto, Masashi ^{[1
]}

Hayase, Shuichi ^{[1
]}

Toh, Toshiyuki ^{[1
]}

机构：

[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan

来源：

TETRAHEDRON | 2008年 / 64卷 / 16期

关键词：

iron catalyst; cobalt catalyst; conjugate addition; enantioselectivity; thiol;

D O I：

10.1016/j.tet.2008.01.121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective conjugate addition of thiols to (E)-3-crotonoyloxazolidin-2-one was effectively catalyzed by the Fe(BF4)(2)center dot 6H(2)O/(S,S)-ip-pybox catalyst. and the addition product was obtained with up to a 95% ee. Furthermore, the CO(ClO4)(2)center dot 6H(2)O/(S,S)-ip-pybox catalyst also catalyzed the same reaction with a high enantioselectivity. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3488 / 3493

页数：6

共 54 条

[1] Highly enantioselective conjugate addition of thiols using mild scandium triflate catalysis [J].

Abe, Aki M. M. ;

Sauerland, Sami J. K. ;

Koskinen, Ari M. P. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5411-5413

[2] Chiral ruthenium PNNP complexes of non-enolized 1,3-dicarbonyl compounds: Acidity and involvement in asymmetric Michael addition [J].

Althaus, Martin ;

Bonaccorsi, Cristina ;

Mezzetti, Antonio ;

Santoro, Francesco .

ORGANOMETALLICS, 2006, 25 (13) :3108-3110

[3]

[Anonymous], COMPREHENSIVE ASYMME

[4]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[5] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[6] Preparation and application of chiral spiro nitrogen-containing ligands for cobalt-catalyzed asymmetric Michael addition [J].

Chen, Chao ;

Zhu, Shou-Fei ;

Wu, Xin-Yan ;

Zhou, Qi-Lin .

TETRAHEDRON-ASYMMETRY, 2006, 17 (19) :2761-2767

[7] L-Proline derived triamine as a highly stereoselective organocatalyst for asymmetric Michael addition of cyclohexanone to nitroolefins [J].

Chen, Halbin ;

Wang, Yu ;

Wei, Siyu ;

Sun, Jian .

TETRAHEDRON-ASYMMETRY, 2007, 18 (11) :1308-1312

[8] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[9]

Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259

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

Dalko, PI ;

Moisan, L .

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

← 1 2 3 4 5 6 →