Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts

被引：1306

作者：

Okino, T ^{[1
]}

Hoashi, Y ^{[1
]}

Takemoto, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 42期

关键词：

PHASE-TRANSFER CATALYSIS; GLYCINATE SCHIFF-BASE; ALPHA-AMINO-ACIDS; CONJUGATE ADDITION; 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC ALKYLATION; NITROALKENES; ALDEHYDES; DERIVATIVES; ALLYLATION;

D O I：

10.1021/ja036972z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Michael reaction of malonates to nitroolefins with chiral bifunctional organocatalysts, bearing both a thiourea and tertiary amino group, afforded Michael adducts with high yields and enantioselectivities (up to 95%, up to 93% ee). Copyright © 2003 American Chemical Society.

引用

页码：12672 / 12673

页数：2

共 47 条

[1] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions
Alexakis, A
Benhaim, C
Rosse, S
Humam, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) : 5262 - 5263
[2] AUDREY O, 2003, ORG LETT, V5, P2559
[3] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram
Barnes, DM
Ji, JG
Fickes, MG
Fitzgerald, MA
King, SA
Morton, HE
Plagge, FA
Preskill, M
Wagaw, SH
Wittenberger, SJ
Zhang, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 13097 - 13105
[4] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[5] Asymmetric catalysis .103. Enantioselective Michael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes
Brunner, H
Kimel, B
[J]. MONATSHEFTE FUR CHEMIE, 1996, 127 (10): : 1063 - 1072
[6] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives
Córdova, A
Watanabe, S
Tanaka, F
Notz, W
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1866 - 1867
[7] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids
Córdova, A
Notz, W
Zhong, GF
Betancort, JM
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1842 - 1843
[8] ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS WITH DIARYLUREAS
CURRAN, DP
KUO, LH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) : 3259 - 3261
[9] Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[10] 2-D

← 1 2 3 4 5 →