Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates

被引：57

作者：

Doyle, MP ^{[1
]}

Valenzuela, M ^{[1
]}

Huang, PL ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2004年 / 101卷 / 15期

关键词：

D O I：

10.1073/pnas.0307025101

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Chiral dirhodium(II) carboxamidates are highly efficient catalysts for reactions between a variety of aldehydes and activated dienes. Catalyst loadings as low at 0.01 mol % have been realized with enantioselectivities up to 97%. Kinetic investigations reveal a pronounced electronic influence on the rate of the hetero-Diels-Alder reaction with a Hammett p value of +11.9 (versus sigma(+)). Inhibition of the catalyst by reactant aldehyde is apparent, but reactions show first-order dependence on aldehyde and diene, and there is a variable dependence on catalyst.

引用

页码：5391 / 5395

页数：5

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