(-)-8-PHENYLMENTHYL ACRYLATE AS CHIRAL INDUCER IN THE BAYLIS-HILLMAN REACTION

被引：26

作者：

DREWES, SE

EMSLIE, ND

KHAN, AA

机构：

[1] Department of Chemistry, University of Natal, Pietermaritzburg, 3200

来源：

SYNTHETIC COMMUNICATIONS | 1993年 / 23卷 / 09期

关键词：

D O I：

10.1080/00397919308011206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

8-Phenylmenthol 1 is used as a chiral auxiliary in the Baylis-Hillman reaction using a range of aldehydes as substrate. Best results (70% d.e.) are obtained when the reaction is rapid, as is the case with trichloroacetaldehyde.

引用

页码：1215 / 1228

页数：14

共 9 条

[1] CHIRAL ACRYLATES AS SUBSTRATES IN BAYLIS-HILLMAN REACTION [J].

BASAVAIAH, D ;

GOWRISWARI, VVL ;

SARMA, PKS ;

RAO, PD .

TETRAHEDRON LETTERS, 1990, 31 (11) :1621-1624

[2] PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].

COREY, EJ ;

ENSLEY, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909

[3] ENANTIOSELECTIVE MICHAEL REACTIONS - STEREOSELECTIVE ADDITION OF ENOLATES OF PHENMENTHOL ESTERS TO CROTONATES [J].

COREY, EJ ;

PETERSON, RT .

TETRAHEDRON LETTERS, 1985, 26 (41) :5025-5028

[4] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS THROUGH HIGH-PRESSURE-INDUCED ADDITION OF AMINES TO ALPHA,BETA-ETHYLENIC ESTERS [J].

DANGELO, J ;

MADDALUNO, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8112-8114

[5] SYNTHESIS, RESOLUTION AND ASSIGNMENT OF ABSOLUTE-CONFIGURATION OF 2-(ALPHA-HYDROXY)ARYL ACRYLATE ESTERS [J].

DREWES, SE ;

EMSLIE, ND ;

FIELD, JS ;

KHAN, AA ;

RAMESAR, N .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :255-260

[6] THE BAYLIS-HILLMAN REACTION-MECHANISM AND APPLICATIONS REVISITED [J].

FORT, Y ;

BERTHE, MC ;

CAUBERE, P .

TETRAHEDRON, 1992, 48 (31) :6371-6384

[7] ASYMMETRIC INDUCTION IN THE BAYLIS-HILLMAN REACTION [J].

GILBERT, A ;

HERITAGE, TW ;

ISAACS, NS .

TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :969-972

[8] FUNCTIONALIZATION OF THE ALPHA-POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL-COMPOUNDS - HIGHLY PRESSURE-DEPENDENT REACTIONS [J].

HILL, JS ;

ISAACS, NS .

TETRAHEDRON LETTERS, 1986, 27 (41) :5007-5010

[9] HIGH ASYMMETRIC INDUCTION IN LEWIS ACID-PROMOTED INTRAMOLECULAR ENE-TYPE REACTIONS - A DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (+)-A-ALLOKAINIC ACID [J].

OPPOLZER, W ;

ROBBIANI, C ;

BATTIG, K .

HELVETICA CHIMICA ACTA, 1980, 63 (07) :2015-2018

← 1 →