Practical stereoselective synthesis of (2E)- and (2Z)-4-cycloalkylidenebut-2-enoic acids

被引：3

作者：

Karagiozov, SK ^{[1
]}

Abbott, FS ^{[1
]}

机构：

[1] Univ British Columbia, Fac Pharmaceut Sci, Div Biomol & Pharmaceut Chem, Vancouver, BC V6T 1Z3, Canada

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 05期

关键词：

Wittig reactions; phosphonate carbanions; stereoselective synthesis; alpha; beta-unsaturated esters; carboxylic acids;

D O I：

10.1081/SCC-120028360

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of alpha,beta-unsaturated esters 7 and 8 was achieved through Homer-Wadsworth-Emmons reaction of beta,beta-disubstituted alpha,beta-unsaturated aldehydes. Thus, aldehydes 6 undergo olefination with phosphonate carbanion generated from triethyl phosphonoacetate 3 and lithium hydroxide or butyl lithium/DMPU to give (E)-alpha,beta-unsaturated esters 7 with excellent selectivity. The treatment of 6 with the new Homer-Emmons reagents, ethyl (diphenylphosphono)acetate 4a and ethyl (di-o-tolyl-phosphono) acetate 4b in the presence of benzyltrimethyl ammonium hydroxide (Triton B) afforded (Z)-alpha,beta-unsaturated

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页码：871 / 888

页数：18

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