Indium mediated γ-pentadienylation of conjugated aldehydes:: synthons for hydrindanes by an oxy-Cope-cycloaddition strategy

被引：20

作者：

Melekhov, A ^{[1
]}

Fallis, AG ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 45期

基金：

加拿大自然科学与工程研究理事会;

关键词：

hydrindanes; indium; intramolecular Diels-Alder reaction;

D O I：

10.1016/S0040-4039(99)01540-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of pentadienylindium to unsaturated aldehydes afforded the alcohols 7, from 1,2-addition, substituted with a 1,4-diene unit. Subsequent anionic oxy-Cope rearrangement provided the Michael 1,4-addition product 8. Wittig reaction followed by intramolecular [2+4] cycloaddition afforded the hydrindane skeleton in an enantioselective manner (five steps). (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：7867 / 7870

页数：4

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