The reductive Nazarov cyclization

被引：41

作者：

Giese, S ^{[1
]}

West, FG ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

基金：

美国国家卫生研究院;

关键词：

annulation; cyclization; dienones; electrocyclic reactions; Nazarov reactions;

D O I：

10.1016/S0040-4039(98)01934-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tri- and tetrasubstituted 1,4-dien-3-ones 1 were treated with Lewis acid in the presence of triethylsilane, furnishing either silyl enol ethers 4 or cyclopentanones 5 in good yields, depending upon work-up conditions. This reaction is presumed to occur through oxyallyl intermediate 3, which undergoes intermolecular hydride transfer and O-silylation to give 4. In most cases, only 2 equiv. of silane was required, and catalytic amounts of Lewis acid could be used. Trienone substrate 7 was found to undergo clean conversion to tricyclic ether 8, indicating fast capture of the oxyallyl intermediate by the pendant olefin. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8393 / 8396

页数：4

共 17 条

[11]

NAZAROV IN, 1950, J GEN CHEM USSR, V20, P1509

[12]

NAZAROV IN, 1959, ZH OBSHCH KHIM+, V29, P1532

[13] TIN-DIRECTED NAZAROV CYCLIZATIONS - A VERSATILE ROUTE TO CYCLOPENTENOIDS [J].