Orthoester condensation/C-O insertion reaction sequence for the preparation of tetrahydrofurans

被引：34

作者：

Calter, MA ^{[1
]}

Sugathapala, PM ^{[1
]}

机构：

[1] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(98)01987-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes a general procedure for the efficient preparation of highly substituted tetrahydrofurans. The condensation of alpha-diazo-beta-ketoester-derived enolates with orthoesters yields diazoacetals la-ld. These compounds undergo formal C-O insertion reactions in the presence of Rh-2(OAc)(4) to afford tetrahydrofurylacetals 2a-2c. Similar insertion reactions of diazoacetals 5a-5d yield bicyclic acetals 6a-6d, which possess cores similar to those of the zaragozic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8813 / 8816

页数：4

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