A NEW METHOD FOR THE SYNTHESIS OF CYCLOPENTENONES VIA THE TANDEM MICHAEL ADDITION-CARBENE INSERTION REACTION OF BETA-KETOETHYNYL(PHENYL)IODONIUM SALTS

被引：84

作者：

WILLIAMSON, BL ^{[1
]}

TYKWINSKI, RR ^{[1
]}

STANG, PJ ^{[1
]}

机构：

[1] UNIV UTAH,DEPT CHEM,SALT LAKE CITY,UT 84112

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 01期

关键词：

D O I：

10.1021/ja00080a011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of substituted 2-cyclopentenones are obtained in good yields (53-82%) via intramolecular 1,5-carbon-hydrogen insertion reactions of [beta-(p-toluenesulfonyl)alkylidene]carbenes derived from Michael addition of sodium p-toluenesulfinate to beta-ketoethynyl(phenyl)iodonium triflates. An extension of the methodology using beta-amidoethynyl(phenyl)iodonium triflates provides a facile synthesis of gamma-lactams including fused bicyclic systems. The isomerization of a substituted cyclopentenone on silica gel is also reported.

引用

页码：93 / 98

页数：6

共 74 条

[1]

ACKROYD M, 1985, HELV CHIM ACTA, V68, P338

[2] SYNTHESIS OF ALKYNYL(PHENYL)IODONIUM TRIFLATES AND THEIR REACTION WITH DIETHYL 2-AMINOMALONATE [J].