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.
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页码：2893 / 2896
页数：4
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