Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine

被引：0

作者：

Key Laboratory of Green Chemistry and Technology , College of Chemistry, Sichuan University, Chengdu 610064, China ^{[1
]}

不详 ^{[2
]}

机构：

[1] Key Laboratory of Green Chemistry and Technology (Sichuan University), College of Chemistry, Sichuan University

[2] State Key Laboratory of Oral Diseases, Sichuan University

来源：

J. Am. Chem. Soc. | 2008年 / 17卷 / 5654-5655期

关键词：

D O I：

10.1021/ja800839w

中图分类号：

学科分类号：

摘要：

Organocatalysts containing primary-secondary amine based on bispidine and amino acid have been designed to catalyze the asymmetric direct aldol reaction of functionalized ketones including α-keto phosphonates, α-keto esters, as well as α,α-dialkoxy ketones as aldol reaction acceptors. The corresponding products with chiral tertiary alcohols were obtained in moderate to high yields (up to 97%) and high enantioselectivities (up to 98% ee). A theoretical study of transition structures demonstrated that protonated piperidine was important for the reactivity and enantioselectivity of this reaction. Copyright © 2008 American Chemical Society.

引用

页码：5654 / 5655

页数：1