Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2022 Feb 4

PMID 35119714

Authors

Cole C Meyer

Zachary J Dubey

Michael J Krische

Affiliations

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Abstract

Cyclometallated iridium-PhanePhos complexes generated in situ from [Ir(cod)Cl] and (R)-PhanePhos catalyze 2-propanol-mediated reductive couplings of 2-substituted dienes with oxetanone and N-acyl-azetidinones to form branched homoallylic oxetanols and azetidinols with excellent control of regio- and enantioselectivity without C-C cleavage of the strained ring via enantiotopic π-facial selection of transient allyliridium nucleophiles. This work represents the first systematic study of enantioselective additions to symmetric ketones.

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