手性二胺催化剂催化2-氧化吲哚对α,β-不饱和酮的非对映发散性催化不对称迈克尔加成反应
Diastereodivergent Catalytic Asymmetric Michael Addition of 2-Oxindoles to α,β-Unsaturated Ketones by Chiral Diamine Catalysts.
作者信息
Wei Yuan, Wen Shigang, Liu Zunwu, Wu Xinxin, Zeng Bubing, Ye Jinxing
机构信息
†Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy and ‡Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
出版信息
Org Lett. 2015 Jun 5;17(11):2732-5. doi: 10.1021/acs.orglett.5b01149. Epub 2015 May 14.
A diastereodivergent catalytic asymmetric Michael addition of 2-oxindoles to α,β-unsaturated ketones has been successfully developed with two complementary chiral diamine catalysts, affording chiral 3,3-disubstituted oxindoles with two adjacent chiral centers. Diastereodivergence has been realized through modifying substrates and utilizing different catalysts. Either anti-or syn-configured products possessing vicinal quaternary and tertiary stereogenic centers were produced with high enantioselectivities.
通过两种互补的手性二胺催化剂，成功开发了一种2-氧化吲哚与α,β-不饱和酮的非对映发散性催化不对称迈克尔加成反应，得到具有两个相邻手性中心的手性3,3-二取代氧化吲哚。通过修饰底物和使用不同的催化剂实现了非对映发散性。具有邻位季碳和叔碳立体中心的反式或顺式构型产物均以高对映选择性得到。
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