Bifunctional Amino Sulfonohydrazide Catalyzed Direct Asymmetric Mannich Reaction of Cyclic Ketimines with Ketones: Highly Diastereo- and Enantioselective Construction of Quaternary Carbon Stereocenter

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• 作者：Sheng Zhang ; Lijun Li ; Yanbin Hu ; Zhenggen Zha ; Zhiyong Wang ; Teck-Peng Loh
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 20, 2015
• 年：2015
• 卷：17
• 期：4
• 页码：1050-1053
• 全文大小：305K
• ISSN：1523-7052

文摘

A bifunctional amino sulfonohydrazide which contains multiple sites for hydrogen bonding with substrates was found to enhance reactivity and enantioselectivity in the direct asymmetric Mannich reaction of N-sulfonyl cyclic ketimines with ketones. In this efficient transformation, not only methyl ketones but also cyclic ketones can be employed to provide a general methodology to construct tetrasubstituted 伪-amino ester in a stereoselective manner. The synthetic utility of a substituted amino ester product is demonstrated by the synthesis of biologically active spirotetrahydrofuran.