A new synthetic approach to 3-methylene-1-cyclohexanols fused to five-, six- and seven-membered carbocycles through intramolecular cyclization of epoxyallylsilanes

被引：0

作者：

Barbero, Asuncion ^{[1
]}

Castreno, Pilar ^{[1
]}

Pulido, Francisco J. ^{[1
]}

Val, Patricia ^{[1
]}

Gonzalez-Ortega, Alfonso ^{[1
]}

Carmen Sanudo, M. ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

ARKIVOC | 2010年

关键词：

Allylsilanes; allenes; silylcupration; epoxyallylsilanes; intramolecular cyclization; methylenecyclohexanols; ACID-CATALYZED CYCLIZATION; MULTIPLE BONDS; SILYLCUPRATION; ALLYLSILANES; ALLENE; ALLYLSTANNANES; CYCLOPENTANE; DERIVATIVES; EPOXIDES; SCOPE;

D O I：

10.3998/ark.5550190.0011.323

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silylcupration of allene followed by conjugate addition to enones and carbonyl epoxidation provides a simple and high yielding route to epoxyallylsilanes carrying the useful phenyldimethylsilyl group. Lewis acid catalyzed intramolecular cyclization of epoxyallylsilanes is a powerful strategy for carbocyclic annulation of much potential in synthesis. In this article we show A general procedure for the synthesis of 3-methylene-1-cyclohexanols fused to five, six and seven-membered carbocycles by intramolecular cyclization of epoxyallylsilanes, which might be of great interest as an approach to bicyclic systems contained in many naturally occurring products, is described.

引用

页码：274 / 287

页数：14

共 20 条

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