1H-吡咯-2,3-二酮与带有多个氢键供体的双功能胺-硫脲催化剂的有机催化不对称亨利反应。
Organocatalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors.
作者信息
Zhang Ming-Liang, Yue Deng-Feng, Wang Zhen-Hua, Luo Yuan, Xu Xiao-Ying, Zhang Xiao-Mei, Yuan Wei-Cheng
机构信息
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; University of Chinese Academy of Sciences, Beijing 100049, China.
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
出版信息
Beilstein J Org Chem. 2016 Feb 16;12:295-300. doi: 10.3762/bjoc.12.31. eCollection 2016.
For the first time, a catalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones was achieved with a chiral bifunctional amine-thiourea as a catalyst possessing multiple hydrogen-bond donors. With this developed method, a range of 3-hydroxy-3-nitromethyl-1H-pyrrol-2(3H)-ones bearing quaternary stereocenters were obtained in acceptable yield (up to 75%) and enantioselectivity (up to 73% ee).
首次实现了以具有多个氢键供体的手性双功能胺-硫脲为催化剂，对1H-吡咯-2,3-二酮进行催化不对称亨利反应。通过这种开发的方法，获得了一系列带有季碳立体中心的3-羟基-3-硝基甲基-1H-吡咯-2(3H)-酮，产率（高达75%）和对映选择性（高达73% ee）均可接受。
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