STEREOCONTROL IN HORNER-WADSWORTH-EMMONS CONDENSATIONS OF A GEM-DIMETHYLCYCLOPROPYL ALDEHYDE WITH ALPHA-SUBSTITUTED PHOSPHONO ACETATES

被引：28

作者：

HAMMOND, GB ^{[1
]}

COX, MB ^{[1
]}

WIEMER, DF ^{[1
]}

机构：

[1] UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 01期

关键词：

D O I：

10.1021/jo00288a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative cleavage of 2-carene provides a keto aldehyde attractive as a synthon for terpenoids containing gem-dimethylcyclopropyl rings. However, the sensitivity of this keto aldehyde to intramolecular aldol condensations proscribes the use of many standard conditions for Wadsworth-Horner-Emmons condensations that might be used to extend this carbon skeleton. Through use of dioxolane-containing phosphono acetates and lithium bases, it is possible to obtain olefin derivatives of this keto aldehyde with reasonable selectivity for either E or Z stereochemistry depending on the choice of phosphonate esters. © 1990, American Chemical Society. All rights reserved.

引用

页码：128 / 132

页数：5

共 27 条

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