Stereoselective synthesis of tetrahydrofurans and tetrahydropyrans by acid-catalyzed cyclization of hydroxy selenides and hydroxy sulfides

被引：28

作者：

Gruttadauria, M ^{[1
]}

Lo Meo, P ^{[1
]}

Noto, R ^{[1
]}

机构：

[1] Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 49期

关键词：

D O I：

10.1016/S0040-4020(99)00876-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The behaviour in acid media of hydroxy selenides and hydroxy sulfides (1a-c and 1'a-c) was investigated. The protection of the primary hydroxyl group in compounds la and 1'a allowed the stereoselective synthesis of a substituted tetrahydrofuran ring, whereas compounds 1b-c and 1'b-c gave an efficient regiochemical control affording substituted tetrahydropyran rings. Tetrahydropyrans containing the phenylselanyl moiety were found to be in equilibrium in the cyclization reaction conditions, whereas tetrahydropyrans containing the phenylsulfanyl moiety were not. A mechanism for the above equilibration is proposed. Semiempirical(AM1, PM3) and ab initio (HF/3-21G*) calculations were used in an attempt to rationalize the experimental results. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14097 / 14110

页数：14

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