J. Am. Chem. Soc., ASAP Article - Asymmetric Direct Aldol Reaction of Functionalized Ketones Catalyzed by Amine Organocatalysts Based on Bispidine
Jie Liu,† Zhigang Yang,† Zhen Wang,† Fei Wang,† Xiaohong Chen,† Xiaohua Liu,† Xiaoming Feng,*†‡ Zhishan Su,† and Changwei Hu*†Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, (Sichuan University), Chengdu 610064, PR China, and State Key Laboratory of Oral Diseases, Sichuan University, Chengdu 610041, PR China
[email]xmfeng@scu.edu.cn[/email]
Received February 11, 2008
Abstract:
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.
[img]http://pubs.acs.org/isubscribe/journals/jacsat/asap/figures/ja-2008-00839w_0005.gif[/img]
[url]http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/asap/abs/ja800839w.html[/url] 四川大学现在风头狠劲嘛，
频频发JACS和Angew，
秦勇（音），冯晓明（音）,一合成，一方法。很牛。
好像还有一个陈应春（音），
现在有多了一个。
[[i] 本帖最后由 yushouyun 于 2008-4-15 23:06 编辑 [/i]]
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