(+)-syn-Benzotriborneol:: the first functionalised enantiopure C3-symmetric benzocyclotrimer

被引：29

作者：

Fabris, F ^{[1
]}

Bellotto, L ^{[1
]}

De Lucchi, O ^{[1
]}

机构：

[1] Univ Ca Foscari Venezia, Dipartimento Chim, I-30123 Venice, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 06期

关键词：

asymmetry; copper and compounds; cyclotrimerisation; cyclotrimers; diastercoselection; stereochemistry; terpenes; triols;

D O I：

10.1016/S0040-4039(02)02789-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I) thiophencarboxylate readily and effectively cyclotrimerises protected 5-bromo-6-trimethylstannylborn-5-en-2-ols, leading to oxygen-functionalised benzocyclotrimers. The remarkably high syn to anti ratio is driven by relative displacement of the halide and metal on the alkene moiety and depends on the steric hindrance of the protecting group of the hydroxy function. The less hindered methyl derivative affords exclusively syn-benzocyclotrimer. The readily removable methoxymethyl derivative gives enantiopure syn-tribenzoborneol in high yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1211 / 1213

页数：3

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