Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates

被引：329

作者：

Ando, K

机构：

[1] College of Education, University of the Ryukyus, Okinawa 903-01, Nishihara-cho

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 07期

关键词：

D O I：

10.1021/jo970057c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New Horner-Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl5, and the corresponding phenols. The reaction of 1 with several kinds of aldehydes in the presence of Triton B or NaH in THF solvent revealed that these reagents are useful far the synthesis of Z-unsaturated esters. Among the reagents examined, ethyl(di-o-tolylphosphono)-, [bis(o-ethylphenyl)phosphono]-, and [bis(o-isopropylphenyl)phosphono]acetate ilk-mi were found to be the most effective, giving Z-unsaturated esters with 93-99% selectivity.

引用

页码：1934 / 1939

页数：6

共 23 条

[1] PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE [J].