Hydrogen bonding control in the oxidative cyclisation of 1,5-dienes

被引：45
作者：
Donohoe, TJ
Winter, JJG
Helliwell, M
Stemp, G
机构：
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
[2] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 06期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/S0040-4039(00)02225-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regioselective dihydroxylation of a series of functionalised polyenes is described. Under acidic conditions, the osmate ester derivatives obtained from oxidation with OsO4/TMEDA undergo an intramolecular cyclisation reaction forming functionalised tetrahydrofurans with high stereoselectivity and in good yield. The generality of this method is illustrated with an application to the synthesis of a bis-tetrahydrofuran ring system. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：971 / 974
页数：4
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