DIRECT AMINO-CROTYLSILYLATION OF ACHIRAL ACETALS AND ALDEHYDES - ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC AMINES AND FUNCTIONALIZED PYRROLIDINES

被引：80

作者：

PANEK, JS

JAIN, NF

机构：

[1] Department of Chemistry, Metcalf Center for Science Engineering, Boston University, Boston

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 10期

关键词：

D O I：

10.1021/jo00089a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation between chiral (E)-crotyl-silanes 1 and in situ-generated achiral N-acylimines produces homoallylic N-acylamines 3 or tetrasubstituted N-acylpyrrolidines 4 with high levels of diastereoselection.

引用

页码：2674 / 2675

页数：2

共 25 条

[1]

BROOK AG, 1980, REARRANGEMENTS GROUN, V2, P190

[2] 5-MEMBERED RING ANNULATION VIA PROPARGYLSILANES AND ALLYLSILANES [J].

DANHEISER, RL ;

DIXON, BR ;

GLEASON, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6094-6097

[3] THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS [J].

HART, DJ ;

HA, DC .

CHEMICAL REVIEWS, 1989, 89 (07) :1447-1465

[4] HIGHLY SELECTIVE AND OPERATIONALLY SIMPLE SYNTHESIS OF ENANTIOMERICALLY PURE BETA-AMINO ESTERS VIA DOUBLE STEREODIFFERENTIATION [J].

HATTORI, K ;

MIYATA, M ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1151-1152

[5] REACTION OF ALLYLSTANNANES WITH ALPHA,BETA-UNSATURATED ACYLIRON COMPLEXES - A NOVEL [3+2] CYCLOADDITION REACTION [J].

HERNDON, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (10) :3165-3166

[6]

Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047

[7]

HOFFMANN RW, 1983, LIEBIGS ANN CHEM, P2000

[8] HOMOALLYLAMINES FROM ALDIMINES AND ALLYLSTANNANES [J].

KECK, GE ;

ENHOLM, EJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (01) :146-147

[9]

KLEINMAN EF, 1991, COMPREHENSIVE ORGANI, V4, P975

[10]

KNOLKER HJ, 1990, SYNLETT, P429

← 1 2 3 →