ADDITION OF ZINC HOMOENOLATES TO ACETYLENIC ESTERS AND AMIDES - A FORMAL [3+2] CYCLOADDITION

被引：45

作者：

CRIMMINS, MT

NANTERMET, PG

TROTTER, BW

VALLIN, IM

WATSON, PS

MCKERLIE, LA

REINHOLD, TL

CHEUNG, AWH

STETSON, KA

DEDOPOULOU, D

GRAY, JL

机构：

[1] Department of Chemistry, The Venable and Kenan Laboratories, University of North Carolina, North Carolina 27599-3290, Chapel Hill

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [(ethoxycyclopropyl)oxy]trimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamido-or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields. The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, alpha,beta-unsaturated esters, acetals, silyl ethers, and furans.

引用

页码：1038 / 1047

页数：10

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