Modular Synthesis of Enantioenriched α‑Chiral Homoallylic Amidines Enabled by Relay Ir/Cu Catalysis

The cascade of Ir-catalyzed enantioselective allylic amination and Cu-catalyzed alkyne–azide cycloaddition was designed for the asymmetric synthesis of homoallylic amidines. The nucleophilic addition of an in situ-generated enantioenriched tertiary allylamine to a ketenimine intermediate triggers a...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2022-09, Vol.24 (37), p.6783-6788
Main Authors: Li, Ting-Peng, Li, Ren-Sha, Hu, Wei, Xie, Jia-Xin, Xu, Minghui, Feng, Chun, Ni, Hai-Liang, Yu, Wen-Hao, Hu, Ping, Wang, Bi-Qin, Cao, Peng
Format: Article
Language:English
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:The cascade of Ir-catalyzed enantioselective allylic amination and Cu-catalyzed alkyne–azide cycloaddition was designed for the asymmetric synthesis of homoallylic amidines. The nucleophilic addition of an in situ-generated enantioenriched tertiary allylamine to a ketenimine intermediate triggers a rapid and stereospecific zwitterionic aza-Claisen rearrangement in a 1,3-chiral transfer manner. The approach allows modular access to enantioenriched α-chiral homoallylic amidines in high yields with a high level of enantiomeric purity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02655