Synthesis of a new versatile dienophile and its use in a highly diastereoselective Diels-Alder reaction

被引：7

作者：

Renaud, JL ^{[1
]}

Aubert, C ^{[1
]}

Malacria, M ^{[1
]}

机构：

[1] Univ Paris 06, Lab Chim Organ Synthese, CNRS, F-75252 Paris 05, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

gibberelins; cyclisation; Diels-Alder reactions; zinc;

D O I：

10.1016/S0040-4039(99)00981-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By using respectively one equivalent of the propargyl zinc alcoholate and silylated propargyl bromide, the preparation of 2-methylene-5-trimethylsilyl-pent-4-yn-1-ol was improved. This latter is the precursor of the corresponding aldehyde which was used for the first time as a dienophile in [4+2] reactions. The cycloadducts were obtained in! very high yields and in a totally diastereoselective manner. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

引用

页码：5015 / 5018

页数：4

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