Asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst

被引：556

作者：

Torii, H

Nakadai, M

Ishihara, K

Saito, S ^{[1
]}

Yamamoto, H

机构：

[1] Nagoya Univ, Inst Adv Res, Nagoya, Aichi 4648602, Japan

[2] Nagoya Univ, Grad Sch Sci, Nagoya, Aichi 4648602, Japan

[3] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

[4] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 15期

关键词：

aldol reaction; amines; asymmetric catalysis; tetrazole; water;

D O I：

10.1002/anie.200352724

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Just add water to improve the performance of direct aldol reactions like that shown. Previously, aldehydes with high water-affinity or -solubility were considered unsuitable for asymmetric synthesis.

引用

页码：1983 / 1986

页数：4

共 60 条

[1] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF CARBOXYLIC-ACID REPLACEMENT ANALOGS OF THE POTENT ANGIOTENSIN CONVERTING ENZYME-INHIBITOR 5(S)-BENZAMIDO-4-OXO-6-PHENYLHEXANOYL-L-PROLINE [J].

ALMQUIST, RG ;

CHAO, WR ;

JENNINGSWHITE, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (08) :1067-1071

[2] Advances in asymmetric enolate methodology [J].

Arya, P ;

Qin, HP .

TETRAHEDRON, 2000, 56 (07) :917-947

[3] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12911-12912

[4] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[5] LEWIS ACID CATALYSIS OF THE ENE ADDITION OF CHLORAL AND BROMAL TO OLEFINS - PRODUCT STUDIES [J].

BENNER, JP ;

GILL, GB ;

PARROTT, SJ ;

WALLACE, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :291-313

[6] Acidity constants of some tetrazole compounds in various aqueous-organic solvent media [J].

Boraei, AAA .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2001, 46 (04) :939-943

[7] Direct organocatalytic aldol reactions in buffered aqueous media [J].

Córdova, A ;

Notz, W ;

Barbas, CF .

CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025

[8] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].

Córdova, A ;

Notz, W ;

Barbas, CF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303

[9] A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF CHIRAL MONOSUBSTITUTED OXIRANES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1993, 34 (33) :5227-5230

[10] A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

COREY, EJ ;

LINK, JO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1906-1908

← 1 2 3 4 5 6 →