Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones

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• 作者：Sheng Zhang ; Lijun Li ; Yanbin Hu ; Yanan Li ; Yu Yang ; Zhenggen Zha ; Zhiyong Wang
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：17
• 期：20
• 页码：5036-5039
• 全文大小：362K
• ISSN：1523-7052

文摘

A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active 尾-amino ketones were directly obtained. More importantly, two different intermediates involved in the reaction were detected and identified by ¹⁹F NMR and HRMS analysis. Furthermore, the synthetic utility of the products was demonstrated by the synthesis of the biologically active fluoroalkyl 尾-amino alcohols.