Direct Asymmetric Hydrogenation and Dynamic Kinetic Resolution of Aryl Ketones Catalyzed by an Iridium‐NHC Exhibiting High Enantio‐ and Diastereoselectivity | Zendy

Ayya Swamy P Chinna | Zendy; Varenikov Andrii | Zendy; Ruiter Graham | Zendy

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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.

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