Organocatalytic asymmetric domino reactions:: A cascade consisting of a Michael addition and an aldehyde α-alkylation

被引：194

作者：

Enders, Dieter ^{[1
]}

Wang, Chuan ^{[1
]}

Bats, Jan W. ^{[2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 39期

关键词：

alkylation; amino acids; domino reactions; organocatalysis; quaternary stereocenters;

D O I：

10.1002/anie.200802532

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A direct approach to cyclic γ-nitroaldehydes with an all-carbon-substituted quaternary stereocenter is provided by a novel organocatalytic diastereo- and enantioselective cascade consisting of a Michael addition and an aldehyde α-alkylation (see scheme). The corresponding γ-amino acids are available in two steps. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7539 / 7542

页数：4

共 114 条

[11] An unexpected organocatalytic asymmetric tandem Michael/Morita-Baylis-Hillman reaction
Cabrera, Silvia
Aleman, Jose
Bolze, Patrick
Bertelsen, Soren
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 121 - 125
[12] CARLONE A, 2007, ANGEW CHEM, V119, P1119
[13] A new approach for an organocatalytic multicomponent domino asymmetric reaction
Carlone, Armando
Cabrera, Silvia
Marigo, Mauro
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) : 1101 - 1104
[14] A simple asymmetric organocatalytic approach to optically active cyclohexenones
Carlone, Armando
Marigo, Mauro
North, Chris
Landa, Aitor
Jorgensen, Karl Anker
[J]. CHEMICAL COMMUNICATIONS, 2006, (47) : 4928 - 4930
[15] Tandem and domino catalytic strategies for enantioselective synthesis
Chapman, Christopher J.
Frost, Christopher G.
[J]. SYNTHESIS-STUTTGART, 2007, (01): : 1 - 21
[16] Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene:: Efficient access to γ2-amino acids
Chi, Yonggui
Guo, Li
Kopf, Nathan A.
Gellman, Samuel H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) : 5608 - +
[17] Organocatalytic asymmetric assembly reactions:: One-pot synthesis of functionalized β-amino alcohols from aldehydes, ketones, and azodicarboxylates
Chowdari, NS
Ramachary, DB
Barbas, CF
[J]. ORGANIC LETTERS, 2003, 5 (10) : 1685 - 1688
[18] Proline-catalyzed asymmetric assembly reactions:: enzyme-like assembly of carbohydrates and polyketides from three aldehyde substrates
Chowdari, NS
Ramachary, DB
Córdova, A
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2002, 43 (52) : 9591 - 9595
[19] Stereoselective construction of quaternary stereocenters
Christoffers, J
Baro, A
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1473 - 1482
[20] Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858

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