A NEW CHIRAL AUXILIARY FOR ASYMMETRIC THERMAL-REACTIONS - HIGH STEREOCONTROL IN RADICAL-ADDITION, ALLYLATION, AND ANNULATION REACTIONS

被引：116

作者：

STACK, JG ^{[1
]}

CURRAN, DP ^{[1
]}

GEIB, SV ^{[1
]}

REBEK, J ^{[1
]}

BALLESTER, P ^{[1
]}

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 18期

关键词：

D O I：

10.1021/ja00044a009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new imide chiral auxiliary, endo-7-(2-benzoxazolyl)-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one(5),is prepared from Kemp's triacid and resolved via its menthyl carbamate. Mixed fumarate derivatives of the auxiliary show unprecedented control of regiochemistry and beta-stereochemistry in representative radical addition reactions. Chiral radicals derived from 5 also show extremely high levels of stereoselectivity in representative radical allylation and cyclization reactions. Structural features of the chiral auxiliary and features of radical addition are integrated into a model for stereoselection.

引用

页码：7007 / 7018

页数：12

共 53 条

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