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

ABSTRACT: Cyclometallated iridium-PhanePhos complexes generated in situ from [Ir(cod)Cl]₂ 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.

SUBMITTER: Meyer CC

PROVIDER: S-EPMC8940717 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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

Meyer Cole C CC Dubey Zachary J ZJ Krische Michael J MJ

Angewandte Chemie (International ed. in English) 20220216 14

Cyclometallated iridium-PhanePhos complexes generated in situ from [Ir(cod)Cl]<sub>2</sub> 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 ...[more]

PMID: 35119714

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