Stereoselective synthesis of tetralins using cationic cyclisations

被引：19

作者：

Appelbe, R

Casey, M ^{[1
]}

Dunne, A

Pascarella, E

机构：

[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

[2] Natl Univ Ireland Univ Coll Dublin, Conway Inst Biomol & Biomed Res, Dublin 4, Ireland

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 41期

关键词：

cationic cyclisations; diastereoselective; tetralins; terpenes; pseudopterosins; calamenenes;

D O I：

10.1016/j.tetlet.2003.08.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetralins, including the terpene calamenene, were prepared by 6-endo cationic cyclisations, effected by addition of an l(l) reagent to alkenylarenes, followed by reductive deiodination. An activating group on the arene was required for efficient cationic cyclisation. Good diastereoselectivity, relative to a chiral centre in the chain linking the alkene to the arene, was observed, with Z-alkenes giving predominantly 1,4-cis disubstituted tetralins, and E-alkenes giving predominantly 1,4-trans derivatives. Analogous 6-exo cationic cyclisations proved very limited in scope. (C) 2003 Elsevier Ltd. All rights reserved.

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收藏

页码：7641 / 7644

页数：4

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