RuO4-catalysed oxidative cyclisation of 1,6-dienes to trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols.: A novel stereoselective process

被引：36

作者：

Piccialli, V ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 19期

关键词：

RuO4; trans-THP diols; stereoselective process;

D O I：

10.1016/S0040-4039(00)00476-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

RuO4 catalyses the stereoselective oxidative cyclisation of the 1,6-dienes, 7-methyl-1,6-octadiene and 1,6-heptadiene, to the corresponding trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols, in the presence of NaIO4 as primary oxidant, in EtOAc:CH3CN:H2O (3:3:1) at 0 degrees C for 4 min. A mechanistic hypothesis explaining the observed trans-2,6-stereochemical control is formulated. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3731 / 3733

页数：3

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