CATALYTIC ASYMMETRIC ALLYLATION REACTIONS .3. EXTENSION TO METHALLYLSTANNANE, COMPARISON OF PROCEDURES, AND OBSERVATION OF A NONLINEAR EFFECT

被引：156

作者：

KECK, GE

KRISHNAMURTY, D

GRIER, MC

机构：

[1] Department of Chemistry, University of Utah, Salt Lake City

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

关键词：

D O I：

10.1021/jo00076a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective additions of methallylstannanes to representative aldehydes with four chiral Lewis acid systems afford ee's of 84-99% using 10 mol % of catalyst. In one case, use of (R)-BINOL of 50% ee gave product with 88% ee.

引用

页码：6543 / 6544

页数：2

共 12 条

[1]

BROWN HC, 1986, J ORG CHEM, V51, P432

[2] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES [J].

COREY, EJ ;

YU, CM ;

KIM, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5495-5496

[3] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

COSTA, AL ;

PIAZZA, MG ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002

[4] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[5]

FURUTA K, 1991, SYNLETT, P561

[6] CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST [J].

FURUTA, K ;

MARUYAMA, T ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1041-1042

[7] CATALYTIC ASYMMETRIC ALLYLATION OF ALDEHYDES [J].

KECK, GE ;

TARBET, KH ;

GERACI, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8467-8468

[8]

KECK GE, 1993, 205TH NAT M AM CHEM

[9]

KECK GE, IN PRESS TETRAHEDRON

[10]

KIRAMURA M, 1989, J AM CHEM SOC, V111, P4028

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