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Highly Enantioselective Iridium(I)‐Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters
Author(s) -
Arribas Andrés,
Calvelo Martín,
Fernández David F.,
Rodrigues Catarina A. B.,
Mascareñas José L.,
López Fernando
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105776
Subject(s) - stereocenter , enantioselective synthesis , iridium , intramolecular force , chemistry , combinatorial chemistry , enantiomer , organocatalysis , catalysis , pyrrole , indole test , stereochemistry , organic chemistry
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.