Asymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds

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• 作者：Ming-Liang Zhang^a ; ^b ; Lin Chen^a ; ^b ; Yong You^a ; ^b ; Zhen-Hua Wang^a ; ^b ; Deng-Feng Yue^a ; ^b ; Xiao-Mei Zhang^a ; Xiao-Ying Xu^a ; ^{xuxy@cioc.ac.cn" class="auth_mail" title="E-mail the corresponding author} ; Wei-Cheng Yuan^a ; ^{yuanwc@cioc.ac.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Asymmetric catalysis ; Organocatalysis ; Michael reaction ; Arylacetyl phosphonates ; Nitroalkenes
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：26 May 2016
• 年：2016
• 卷：72
• 期：21
• 页码：2677-2682
• 全文大小：605 K

文摘

Catalytic asymmetric Michael addition of arylacetyl phosphonates to nitroalkenes was achieved with a chiral bifunctional amine-thiourea bearing a multiple-hydrogen-bond donor as a catalyst. A range of α-substituted carboxylic ester compounds with contiguous tertiary stereocenters could be smoothly obtained in good yields (up to 85%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 95% ee). The large scale experiment and facile synthesis of a chiral γ-butyrolactam have also been demonstrated.