通过[1,2]-磷-Brook重排实现的手性路易斯酸催化的不对称多组分迈克尔反应
Chiral Lewis Acid-Catalyzed Asymmetric Multicomponent Michael Reaction through [1,2]-Phospha-Brook Rearrangement.
作者信息
Lin Qianchi, Wang Siyuan, Weng Rui, Cao Weidi, Feng Xiaoming
机构信息
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
出版信息
Org Lett. 2023 Sep 1;25(34):6262-6266. doi: 10.1021/acs.orglett.3c02042. Epub 2023 Aug 21.
The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and 4-oxobutenoates was realized. A series of oxindole derivatives containing two contiguous stereocenters was obtained in high yields and excellent stereoselectivities (up to >99% yield, >95:5 dr, >99% ee) using a chiral Lewis acid catalyst. A possible catalytic model is presented to illustrate the stereocontrol.
实现了异吲哚酮、亚磷酸酯和4-氧代巴豆酸酯的多组分催化不对称普多维克加成/[1,2]-磷杂-布鲁克重排/迈克尔反应序列。使用手性路易斯酸催化剂，以高收率和优异的立体选择性（收率高达>99%，非对映体比例>95:5，对映体过量>99%）得到了一系列含有两个相邻立体中心的氧化吲哚衍生物。提出了一个可能的催化模型以说明立体控制。
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