Experimental and computational studies of nucleophilic additions of metal hydrides and organometallics to hindered cyclohexanones

被引：29

作者：

Ando, K

Houk, KN

Busch, J

Menassé, A

Séquin, U

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Univ Basel, Inst Organ Chem, CH-4056 Basel, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 06期

关键词：

D O I：

10.1021/jo9616116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistries of nucleophilic additions of several hydride, methyl, and acetylenic Grignard and lithium reagents to hindered cyclohexanones were investigated experimentally. Acetylenic reagents attack hindered cyclohexanones from the axial direction, in contrast to the result with other reagents. Ab initio calculations and a modified MM2 transition-state force field were used to study the origins of stereoselectivity.

引用

页码：1761 / 1766

页数：6

共 31 条

[1] STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES [J].