How to make five contiguous stereocenters in one reaction: Asymmetric organocatalytic synthesis of pentasubstituted cyclohexanes

被引：128

作者：

Reyes, Efraim ^{[1
]}

Jiang, Hao ^{[1
]}

Milelli, Andrea ^{[1
]}

Elsner, Petteri ^{[1
]}

Hazell, Rita G. ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Ctr Catalysis, Danish Natl Res Fdn, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 48期

关键词：

alpha; beta-unsaturated aldehydes; asymmetric synthesis; domino reaction; nucleophilic addition; organocatalysis;

D O I：

10.1002/anie.200704454

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Give me five! An organocatalyzed two-component domino reaction has been developed in which two new C-C bonds and five stereocenters are created in a one-pot fashion (see scheme; DABCO = 1,4-diazabicyclo[2.2.2]octane, TMS = trimethylsilyl). The striking features of this transformation are the high preference for one diastereomer (out of 32 possible isomers) and enantioselectivities of up to 94 %. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9202 / 9205

页数：4

共 75 条

[1]

[Anonymous], 2004, ANGEW CHEM, V116, P1292

[2]

[Anonymous], 1999, COMPREHENSIVE ASYMME

[3] Practical asymmetric henry reaction catalyzed by a chiral Diamine-Cu(OAc)2 complex [J].

Arai, Takayoshi ;

Watanabe, Masahiko ;

Yanagisawa, Akira .

ORGANIC LETTERS, 2007, 9 (18) :3595-3597

[4] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A ;

Petrini, M .

CHEMICAL REVIEWS, 2005, 105 (03) :933-971

[5] One-pot synthesis of 1,3-dinitroalkanes under heterogeneous catalysis [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A .

SYNTHESIS-STUTTGART, 2004, (12) :1938-1940

[6] Catalytic asymmetric Henry reaction [J].

Boruwa, Joshodeep ;

Gogoi, Naminita ;

Saikia, Partha Pratim ;

Barua, Nabin C. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (24) :3315-3326

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

Bui, T ;

Barbas, CF .

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

[8]

CARDANI S, 1992, TETRAHEDRON, V48, P5557

[9]

CARLONE A, 2007, ANGEW CHEM, V119, P1119

[10] A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].

Carlone, Armando ;

Cabrera, Silvia ;

Marigo, Mauro ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104

← 1 2 3 4 5 6 7 8 →