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
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.
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收藏
页码:8813 / 8816
页数:4
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