Organocatalytic transformation of 1,3-diketones into optically active cyclohexanones

被引：46

作者：

Gryko, D ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 07期

关键词：

D O I：

10.1016/j.tetasy.2005.02.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The domino Michael-aldol reaction of 1,3-diketones with MVK in the presence of L-proline furnished highly substituted cyclohexanones in a regio- and stereocontrolled manner. When the reaction was performed in NMP, high yields (up to 93%) and enantioselectivities up to 80% were observed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1377 / 1383

页数：7

共 39 条

[1] Organocatalytic enantioselective conjugate addition to alkynones [J].

Bella, M ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5672-5673

[2]

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

[3] Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].

Bogevig, A ;

Sundén, H ;

Córdova, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1109-1112

[4]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

[5]

2-Y

[6] The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].

Brown, SP ;

Brochu, MP ;

Sinz, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809

[7] A proline-catalyzed asymmetric Robinson annulation reaction [J].

Bui, T ;

Barbas, CF .

TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954

[8]

*CCDC, 253670 CCDC

[9] Novel chemoselective and diastereoselective iron(III)-catalysed Michael reactions of 1,3-dicarbonyl compounds and enones [J].

Christoffers, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3141-3149

[10] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives [J].

Córdova, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) :1987-1997

← 1 2 3 4 →