Catalytic asymmetric Mukaiyama aldol reactions in aqueous media

被引：110

作者：

Kobayashi, S ^{[1
]}

Nagayama, S ^{[1
]}

Busujima, T ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

D O I：

10.1016/S0040-4020(99)00440-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral copper(II)-catalyzed asymmetric aldol reactions of silyl enol ethers with aldehydes (the Mukaiyama aldol reaction) have been performed in an ethanol-water solution. The use of the protic solvent including water is a key to achieve these reactions. Moreover, a catalytic asymmetric aldol reaction in pure water without using organic solvents has also been successfully carried out. This report has proposed and demonstrated a new concept for solvents in catalytic asymmetric aldol reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8739 / 8746

页数：8

共 47 条

[1] CATALYTIC ENANTIOSELECTIVE C-C COUPLING - ALLYL TRANSFER AND MUKAIYAMA ALDOL REACTION
BACH, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04): : 417 - 419
[2] ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE WITH RHODIUM OXAZOLINES CATALYSTS
BALAVOINE, G
CLINET, JC
LELLOUCHE, I
[J]. TETRAHEDRON LETTERS, 1989, 30 (38) : 5141 - 5144
[3] ASYMMETRIC CATALYSIS .45. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2/PYRIDINYLOXAZOLINE CATALYSTS
BRUNNER, H
OBERMANN, U
[J]. CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (03): : 499 - 507
[4] METAL VERSUS SILYL TRIFLATE CATALYSIS IN THE MUKAIYAMA ALDOL ADDITION-REACTION
CARREIRA, EM
SINGER, RA
[J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4323 - 4326
[5] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV)
CARREIRA, EM
SINGER, RA
LEE, WS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8837 - 8838
[6] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX
COREY, EJ
IMAI, N
ZHANG, HY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 728 - 729
[7] COTTON FA, 1988, ADV INORG CHEM, pH18
[8] The chemistry of trichlorosilyl enolates .2. Highly-selective asymmetric aldol additions of ketone enolates
Denmark, SE
Wong, KT
Stavenger, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2333 - 2334
[9] TRIARYLCARBENIUM IONS AS CATALYSTS IN THE MUKAIYAMA ALDOL ADDITION - A MECHANISTIC INVESTIGATION
DENMARK, SE
CHEN, CT
[J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4327 - 4330
[10] EINHORN C, 1989, SYNTHESIS-STUTTGART, P787

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