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有机催化的区域和对映选择性烯丙基烷基化吲哚啉-2-亚胺与 MBH 碳酸盐,得到 3-烯丙基吲哚。

Organocatalytic Regio- and Enantioselective Allylic Alkylation of Indolin-2-imines with MBH Carbonates toward 3-Allylindoles.

机构信息

School of Resources and Environment, Harbin Institute of Technology, Harbin 150080, China.

Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology (SUSTech), Shenzhen 518055, China.

出版信息

J Org Chem. 2023 Jun 16;88(12):7810-7814. doi: 10.1021/acs.joc.2c02310. Epub 2023 Jan 26.

Abstract

An organocatalytic asymmetric C3-allylic alkylation of indolone-2-imines with MBH carbonates has been developed for the first time. As opposed to previous reports, an "interrupted" annulation was achieved, affording 3-allylindoles in generally high yields with excellent stereoselectivities. The representative scale-up reaction and transformation of 3-allylindoles were examined. A possible mechanism was also proposed.

摘要

首次发展了一种有机催化的不对称 C3-烯丙基烷基化吲哚啉-2-亚胺与 MBH 碳酸盐的反应。与以前的报道不同,实现了“中断”的环化反应,以通常高的收率和优异的立体选择性得到 3-烯丙基吲哚。考察了代表性的放大反应和 3-烯丙基吲哚的转化。还提出了一种可能的反应机制。

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