Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine

被引：240

作者：

Andrey, O ^{[1
]}

Alexakis, A ^{[1
]}

Bernardinelli, G ^{[1
]}

机构：

[1] Univ Geneva, CH-1211 Geneva, Switzerland

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 14期

关键词：

D O I：

10.1021/ol0348755

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The regio-, stereo-, and enantioselective direct Michael addition of alpha-hydroxyketones to beta-aryinitroolef ins catalyzed by N-/Pr-2,2'-bipyrrolidine is described. The formation of an internal hydrogen bond between the OH group of alpha-hydoxyacetone and the tertiary nitrogen of the catalyst leads to the formation of a rigid cis enamine intermediate that explains the inversion of the expected diastereoselectivity and the very high ee's.

引用

页码：2559 / 2561

页数：3

共 41 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
[2] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
[3] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
Betancort, JM
Barbas, CF
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
[4] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
Betancort, JM
Sakthivel, K
Thayumanavan, R
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2001, 42 (27) : 4441 - 4444
[5] ASYMMETRIC MICHAEL ADDITIONS - REGIO-SELECTIVE, DIASTEREO-SELECTIVE, AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINES FROM BETA-TETRALONES AND (S)-2-(METHOXYMETHYL)PYRROLIDINE (PROLINOL METHYL-ETHER) BY OMEGA-NITROSTYRENES
BLARER, SJ
SEEBACH, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (09): : 3086 - 3096
[6] Direct catalytic asymmetric aldol reactions of aldehydes
Bogevig, A
Kumaragurubaran, N
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
[7] Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO
[8] 2-Y
[9] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture
Brown, SP
Goodwin, NC
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) : 1192 - 1194
[10] 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

← 1 2 3 4 5 →