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

被引：110

作者：

Liu, Jie ^{[1
]}

Yang, Zhigang ^{[1
]}

Wang, Zhen ^{[1
]}

Wang, Fei ^{[1
]}

Chen, Xiaohong ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
,2
]}

Su, Zhishan ^{[1
]}

Hu, Changwei ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Sichuan Univ, State Key Lab Oral Dis, Chengdu 610041, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 17期

关键词：

D O I：

10.1021/ja800839W

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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 alpha-keto phosphonates, alpha-keto esters, as well as alpha,alpha-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.

引用

页码：5654 / +

页数：3

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