OsO4-catalyzed oxidative cyclization of geranyl and neryl acetate to cis-2,5-bis(hydroxymethyl)tetrahydrofurans

被引：64

作者：

de Champdoré, M ^{[1
]}

Lasalvia, M ^{[1
]}

Piccialli, V ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Organ & Biol, I-80134 Naples, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 52期

关键词：

1,5-dienes; OsO[!sub]4[!/sub; Oxidative cyclization; THF;

D O I：

10.1016/S0040-4039(98)02172-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

OsO4 catalyzes the oxidative cyclization of the 1,5-dienes geranyl acetate (1) and neryl acetate (2) to the cis-2,5-bis(hydroxymethyl)tetrahydrofurans 3 and 4 respectively, in the presence of NaIO4 as cooxidant in DMF. The reaction is stereospecific and proceeds with the sequential syn addition to both double bonds of the starting materials. The observed stereoselectivity can be explained by invoking the intermediacy of a square based pyramidal osmium (VI) diester (5) that has been isolated and characterized. Evidence is reported that this substance is indeed an intermediate in the transformation of 1 to 3. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9781 / 9784

页数：4

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