Stereoselective syntheses of beta,gamma-unsaturated esters and gamma-lactones: 1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a protected =CCH2CO2Et synthon equivalent

被引：11

作者：

Katritzky, AR

Feng, DM

Lang, HY

机构：

[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 12期

关键词：

D O I：

10.1021/jo9701647

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.

引用

页码：4131 / 4136

页数：6

共 33 条

[21] A NOVEL HETEROCYCLE-STABILIZED ALLYLIC ANION ROUTE TO CYCLOPROPANES, 1-ETHOXY-1-VINYLETHYLENE OXIDES, 1-HYDROXYALKYL 2-METHOXYETHYL KETONES, 1-HYDROXYALKYL VINYL KETONES, BETA-ETHOXY-BETA-VINYLALKYL ALCOHOLS, GAMMA-LACTONES, AND BETA,GAMMA-UNSATURATED CARBOXYLIC-ACIDS [J].