Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis:: A highly enantioselective route to β-amino acids

被引：143

作者：

Ibrahem, Ismail ^{[1
]}

Rios, Ramon ^{[1
]}

Vesely, Jan ^{[1
]}

Zhao, Gui-Ling ^{[1
]}

Cordova, Armando ^{[1
]}

机构：

[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

CHEMICAL COMMUNICATIONS | 2007年 / 08期

关键词：

D O I：

10.1039/b613410f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly chemo- and enantioselective organocatalytic tandem reaction between N-protected hydroxyl amines and a, beta-unsaturated aldehydes is presented; the reaction provides access to 5-hydroxyisoxazolidines and beta-amino acids in high yields and with 90-99% ee.

引用

页码：849 / 851

页数：3

共 41 条

[1] A GENERAL PROCEDURE FOR THE SYNTHESIS OF ISOXAZOLIDIN-5-ONES [J].

BALDWIN, JE ;

HARWOOD, LM ;

LOMBARD, MJ .

TETRAHEDRON, 1984, 40 (21) :4363-4370

[2] Enantioselective organocatalytic amine conjugate addition [J].

Chen, Young K. ;

Yoshida, Masanori ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9328-9329

[3]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[4]

2-D

[5] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[6] Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates [J].

Doi, H ;

Sakai, T ;

Iguchi, M ;

Yamada, K ;

Tomioka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2886-2887

[7] Proline-catalyzed asymmetric α-amination of aldehydes and ketones -: An astonishingly simple access to optically active α-hydrazino carbonyl compounds [J].

Duthaler, RO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :975-978

[8] Control of four stereocentres in a triple cascade organocatalytic reaction [J].

Enders, Dieter ;

Hüettl, Matthias R. M. ;

Grondal, Christoph ;

Raabe, Gerhard .

NATURE, 2006, 441 (7095) :861-863

[9]

GRAF E, 1958, LIEBIGS ANN CHEM, V613, P111

[10] Highly enantio- and diastereoselective organocatalytic asymmetric domino Michael-Aldol reaction of β-ketoesters and α,β-unsaturated ketones [J].

Halland, N ;

Aburel, PS ;

Jorgensen, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1272-1277

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