Asymmetric Dearomatization of Indole by Palladium/PC-Phos-Catalyzed Dynamic Kinetic Transformation

被引：64

作者：

Chu, Haoke ^{[1
]}

Cheng, Jie ^{[2
]}

Yang, Junfeng ^{[1
]}

Guo, Yin-Long ^{[2
]}

Zhang, Junliang ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Stake Key Lab Organometall Chem, Shanghai, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 49期

关键词：

alkynes; catalytic asymmetric dearomatization; chiral spiroindolenine; dynamic kinetic transformation; palladium; ENANTIOSELECTIVE CONSTRUCTION; ALLYLIC DEAROMATIZATION; SPIROCYCLIC OXINDOLES; HIGHLY EFFICIENT; CASCADE; REDUCTION; ACCESS; SPIROINDOLENINES; CYCLOADDITIONS; RACEMIZATION;

D O I：

10.1002/anie.202010164

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3 '-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.

引用

页码：21991 / 21996

页数：6

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