Carbohydrate-Templated Asymmetric Diels-Alder Reactions of Masked ortho-Benzoquinones for the Synthesis of Chiral Bicyclo[2.2.2]oct-5-en-2-ones

被引：40
|
作者：
Luo, Shun-Yuan [1 ]
Jang, Yeong-Jiunn [1 ]
Liu, Jing-Yuan [1 ]
Chu, Chrong-Shyua [1 ]
Liao, Chun-Chen [1 ]
Hung, Shang-Cheng [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 42期
关键词：
asymmetric synthesis; benzoquinones; bicyclic compounds; chiral auxiliaries; cycloaddition;
D O I：
10.1002/anie.200802693
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) A sweet addition: Asymmetric [4 + 2] cycloaddition of masked ortho-benzoquinones with various alkenols by using sugars as chiral auxiliaries (see scheme; Bn: benzyl) affords the optically pure bicyclo[2.2.2]oct-5-en-2-ones with excellent diastereoselectivity and in good yields. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：8082 / 8085
页数：4
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