Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 35, Pages 19297-19305Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202105776
Keywords
C-H activation; enantioselective; heterocycles; hydrocarbonation; iridium
Categories
Funding
- Spanish MINECO [SAF2016-76689-R, PID2019-108624RB-I00, CTQ2017-84767-P, PID2020-118579GB-I00]
- Xunta de Galicia [ED431C 2017/19, 2015-CP082, ED431G 2019/03, ED481B-2019-005]
- ERDF, ERC [340055]
Ask authors/readers for more resources
The study presents a versatile and highly enantioselective intramolecular hydrocarbonation reaction for the synthesis of heteropolycyclic systems with chiral quaternary carbon stereocenters. The method relies on an iridium-(I)/bisphosphine chiral catalyst, yielding fused indole and pyrrole products with high enantiomeric excesses. DFT computational studies provided a detailed mechanistic profile and identified weak non-covalent interactions as key factors controlling the enantioselectivity.
We report a versatile, highly enantioselective intramolecular hydrocarbonation reaction that provides a direct access to heteropolycyclic systems bearing chiral quaternary carbon stereocenters. The method, which relies on an iridium-(I)/bisphosphine chiral catalyst, is particularly efficient for the synthesis of five-, six- and seven-membered fused indole and pyrrole products, bearing one and two stereocenters, with enantiomeric excesses of up to >99%. DFT computational studies allowed to obtain a detailed mechanistic profile and identify a cluster of weak non-covalent interactions as key factors to control the enantioselectivity.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available