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Direct Asymmetric Hydrogenation and Dynamic Kinetic Resolution of Aryl Ketones Catalyzed by an Iridium‐NHC Exhibiting High Enantio‐ and Diastereoselectivity
Author(s) -
Ayya Swamy P Chinna,
Varenikov Andrii,
Ruiter Graham
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904911
Subject(s) - kinetic resolution , iridium , oxazoline , catalysis , aryl , carbene , chemistry , combinatorial chemistry , ketone , asymmetric hydrogenation , noyori asymmetric hydrogenation , enantioselective synthesis , organic chemistry , alkyl
A chiral iridium carbene‐oxazoline catalyst is reported that is able to directly and efficiently hydrogenate a wide variety of ketones in excellent yields and good enantioselectivity (up to 93 % ee ). Moreover, when using racemic α‐substituted ketones, excellent diastereoselectivities were obtained ( dr 99:1) by dynamic kinetic resolution of the in situ formed enolate. Overall, the herein described hydrogenation occurs under ambient conditions using low hydrogen pressures, providing a direct and atom efficient method towards chiral secondary alcohols.