Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions

被引：19

作者：

Evanno, Laurent

Deville, Alexandre

Dubost, Lionel

Chiaroni, Angele

Bodo, Bernard

Nay, Bastien

机构：

[1] CNRS, Museum Natl Hist Nat, Lab Chim & Biochim Subst Nat, F-75005 Paris, France

[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 16期

关键词：

Diels-Alder reaction; stereoselectivity; Z-diene; endo-boat; transition state; total synthesis;

D O I：

10.1016/j.tetlet.2007.02.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ethylidene acetal Of D-erythrose was used as a template for stereoselective IMDA reactions: high endo selectivity and yields in favor of the cis product were observed with 1,3,9-trienes, resulting from a boat transition state. For natural product synthesis, the reaction was successfully applied to a diene with terminal Z-olefin. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2893 / 2896

页数：4

共 29 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2] STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .3. A POTENTIALLY GENERAL-METHOD FOR THE SYNTHESIS OF CIS-HYDRINDENES BY USE OF (Z)-DIENE UNITS [J].