Organocatalytic Asymmetric Michael Addition of 3-Pyrrolyloxindoles to β-Phthalimidonitroethene for the Synthesis of 3,3′-Disubstituted Oxindoles Bearing Contiguous 3,α,β-Triamino Functionality

详细信息    查看全文

• 作者：Yong You ; Zhi-Jun Wu ; Jian-Feng Chen ; Zhen-Hua Wang ; Xiao-Ying Xu ; Xiao-Mei Zhang ; Wei-Cheng Yuan
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：81
• 期：13
• 页码：5759-5765
• 全文大小：476K
• 年卷期：0
• ISSN：1520-6904

文摘

An organocatalytic asymmetric Michael addition reaction of 3-pyrrolyloxindoles to β-phthalimidonitroethene has been developed with a bifunctional thiourea–tertiary amine as the catalyst. A range of 3,3′-disubstituted oxindoles bearing contiguous 3,α,β-triamino functionality could be obtained in high yields with good diastereoselectivities and high enantioselectivities (up to 99% yield, 99:1 dr, and 98% ee). The higher reactivity of β-phthalimidonitroethene compared to the reactivity of ordinary nitroalkenes in the reaction with 3-pyrrolyloxindoles was demonstrated by contrast experiments.