Tandem Catalytic Indolization/Enantioconvergent Substitution of Alcohols by Borrowing Hydrogen to Access Tricyclic Indoles

An efficient tandem catalysis method is achieved for the direct conversion of alcohol‐containing alkynyl anilines to valuable chiral 2,3‐fused tricyclic indoles. This method relies on a tandem indolization followed by enantioconvergent substitution of alcohols via borrowing hydrogen to construct two...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-09, Vol.60 (38), p.20689-20694
Main Authors: Yang, Guoqiang, Pan, Jiaoting, Ke, Ya‐Ming, Liu, Yongbing, Zhao, Yu
Format: Article
Language:English
Subjects:
Alcohols
Aniline
Catalysis
Direct conversion
enantioselectivity
hydrogen
Indoles
Iridium
Iridium compounds
Phosphoric acid
redox-neutral catalysis
relay catalysis
Stereoselectivity
Substitutes
tricyclic indoles
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient tandem catalysis method is achieved for the direct conversion of alcohol‐containing alkynyl anilines to valuable chiral 2,3‐fused tricyclic indoles. This method relies on a tandem indolization followed by enantioconvergent substitution of alcohols via borrowing hydrogen to construct two rings in one step, enabled by relay and cooperative catalysis of a chiral iridium complex with a chiral phosphoric acid. Highly diastereoselective transformations of the tricyclic indole products also provide efficient access to a diverse array of complex polycyclic indoline compounds. An efficient indolization/enantioconvergent borrowing hydrogen cascade is achieved for the construction of chiral 2,3‐fused tricyclic indoles, enabled by relay and cooperative catalysis of a chiral iridium complex with a chiral phosphoric acid. Highly diastereoselective transformations of the tricyclic indole products also provide efficient access to a diverse array of complex polycyclic indolines.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202106514