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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.

DOI:10.3762/bjoc.12.31
PMID:26977188
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4778496/
Abstract

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).

摘要

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。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/67a37f228b11/Beilstein_J_Org_Chem-12-295-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/ebbb0809376a/Beilstein_J_Org_Chem-12-295-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/1319d1cbf5e8/Beilstein_J_Org_Chem-12-295-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/67a37f228b11/Beilstein_J_Org_Chem-12-295-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/ebbb0809376a/Beilstein_J_Org_Chem-12-295-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/1319d1cbf5e8/Beilstein_J_Org_Chem-12-295-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1923/4778496/67a37f228b11/Beilstein_J_Org_Chem-12-295-g003.jpg

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