CATALYTIC ASYMMETRIC ALDOL-TYPE REACTION USING A CHIRAL TIN(II) LEWIS ACID

被引：96

作者：

KOBAYASHI, S

UCHIRO, H

SHIINA, I

MUKAIYAMA, T

机构：

[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Shinjuku-ku, Tokyo, 162, Kagurazaka

来源：

TETRAHEDRON | 1993年 / 49卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)80533-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly diastereo- and enantioselective aldol-type reactions of a silyl enol ether with aldehydes including aromatic, aliphatic, and alpha,beta-unsaturated ones are performed in propionitrile (solvent) by the use of a catalytic amount of chiral tin(II) Lewis acid consisting of tin(II) triflate and a chiral diamine. The asymmetric environments created by the chiral catalysts in the enantioselective aldol reaction are discussed by employing five kinds of chiral diamines.

引用

页码：1761 / 1772

页数：12

共 85 条

[1] ALDOL CONDENSATIONS OF CHIRAL ALPHA-HALOIMIDATES - A CHIRAL DARZENS CONDENSATION PROCEDURE
ABDELMAGID, A
LANTOS, I
PRIDGEN, LN
[J]. TETRAHEDRON LETTERS, 1984, 25 (31) : 3273 - 3276
[2] SYNTHESIS OF BRYOSTATINS .1. CONSTRUCTION OF THE C(1)-C(16) FRAGMENT
BLANCHETTE, MA
MALAMAS, MS
NANTZ, MH
ROBERTS, JC
SOMFAI, P
WHRITENOUR, DC
MASAMUNE, S
KAGEYAMA, M
TAMURA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) : 2817 - 2825
[3] ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES
BONNER, MP
THORNTON, ER
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1299 - 1308
[4] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM
COREY, EJ
IMWINKELRIED, R
PIKUL, S
XIANG, YB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5493 - 5495
[5] VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS
COREY, EJ
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) : 4976 - 4977
[6] CHIRAL PROPIONATE ENOLATE EQUIVALENTS FOR THE STEREOSELECTIVE SYNTHESIS OF THREO-ALPHA-METHYL-BETA-HYDROXY OR ERYTHRO-ALPHA-METHYL-BETA-HYDROXY ACIDS
DAVIES, SG
DORDORHEDGECOCK, IM
WARNER, P
[J]. TETRAHEDRON LETTERS, 1985, 26 (17) : 2125 - 2128
[7] ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .2. ENANTIOSELECTIVE ALDOL REACTION OF TERT-BUTYL ACETATE USING TITANIUM-CARBOHYDRATE COMPLEXES
DUTHALER, RO
HEROLD, P
LOTTENBACH, W
OERTLE, K
RIEDIKER, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04): : 495 - 497
[8] ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .5. ENANTIOSELECTIVE AND DIASTEREOSELECTIVE ALDOL-REACTION OF 2,6-DIMETHYLPHENYL PROPIONATE USING TITANIUM-CARBOHYDRATE COMPLEXES
DUTHALER, RO
HEROLD, P
WYLERHELFER, S
RIEDIKER, M
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (03) : 659 - 673
[9] REGIOSPECIFIC AND ENANTIOSELECTIVE ALDOL REACTIONS
EICHENAUER, H
FRIEDRICH, E
LUTZ, W
ENDERS, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (03): : 206 - 208
[10] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDOL REACTIONS VIA ALPHA-SILYL KETONES, ASYMMETRIC-SYNTHESIS OF THE AGGREGATION PHEROMONE SITOPHILURE
ENDERS, D
LOHRAY, BB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (04): : 581 - 583

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