Enantioselective bronsted acid catalyzed conjugate addition of aryl methyl ketone derived enamines to nitroalkenes

被引：24

作者：

Dixon, DJ

Richardson, RD

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] Univ Cambridge, Chem Labs, Cambridge CB2 1EW, England

来源：

SYNLETT | 2006年 / 01期

关键词：

Bronsted acid; organocatalysis; nitroalkene; thiourea; enantioselective;

D O I：

10.1055/s-2005-922776

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Bronsted acid catalyst has been developed for the conjugate addition of aryl methyl ketone derived enamines to nitroalkenes in good yield and moderate enantioselectivity.

引用

页码：81 / 85

页数：5

共 48 条

[41] Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding [J].

Unni, AK ;

Takenaka, N ;

Yamamoto, H ;

Rawal, VH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1336-1337

[42] Chiral Bronsted acid-catalyzed direct Mannich reactions via electrophilic activation [J].

Uraguchi, D ;

Terada, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) :5356-5357

[43] Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction [J].

Vachal, P ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10012-10014

[44] Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes [J].

Wang, W ;

Wang, J ;

Li, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1369-1371

[45] Asymmetric catalytic Mannich reactions catalyzed by urea derivatives:: Enantioselective synthesis of β-aryl-β-amino acids [J].

Wenzel, AG ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :12964-12965

[46] Highly enantioselective thiourea-catalyzed nitro-Mannich reactions [J].

Yoon, TP ;

Jacobsen, EN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :466-468

[47] A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions [J].

Zhuang, W ;

Poulsen, TB ;

Jorgensen, KA .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (18) :3284-3289

[48] Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst -: synthesis of optically active tetrahydro-β-carbolines [J].

Zhuang, W ;

Hazell, RG ;

Jorgensen, KA .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (14) :2566-2571

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