P-225,917 synthetic studies: unusual hydroboration regioselectivity influenced by remote functional groups

被引：11

作者：

Ashenhurst, James A. ^{[1
]}

Gleason, James L. ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2007.11.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroboration-oxidation of 1,1-disubstituted alkenes with borane-methyl sulfide complex in bridged tricyclic intermediates of the CP-225.917 ring system were observed to produce significant quantities of tertiary alcohol products. This net Markovnikov addition of water across an alkene is influenced by a combination of remote functional groups. Computations at the B3LYP/6-31G* level of theory correctly predicted this reversal in selectivity and directed the selective removal of functional groups to restore selectivity for the primary alcohol. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：504 / 507

页数：4

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