N-Heterocyclic Carbene-Catalyzed Activation of Esters of N-Hydroxyphthalimide: A Highly Enantioselective Route to Chiral Dihydropyridinones Bearing an All Carbon Quaternary Stereogenic Center

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• 作者：Zhiming Zhang ; Xiaofei Zeng ; Danbo Xie ; Dongdong Chen ; Liyuan Ding ; Anna Wang ; Limin Yang ; Guofu Zhong
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：17
• 期：20
• 页码：5052-5055
• 全文大小：399K
• ISSN：1523-7052

文摘

An N-heterocyclic carbene-catalyzed highly enantioselective [3 + 3] annulation reaction of N-hydroxyphthalimide (NHPI) 3,3-disubstituted acrylates and N-Ts ketimines was developed. In most cases, the desired chiral dihydropyridinone products bearing an all carbon quaternary stereogenic center could be obtained in good yields with excellent enantioselectivities (>99% ee鈥檚), which demonstrated the NHPI acrylates as a kind of excellent substrate in NHC-catalysis.