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

页码：8082 / 8085

页数：4

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