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Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes.

ABSTRACT: Oxime-directed catalytic asymmetric hydroboration is diverted to catalytic asymmetric hydrogenation (CAH) upon the addition of a proton source, such as MeOH, or by running the reaction under a hydrogen atmosphere. A borane (e.g., pinacolborane) is required to promote CAH. Tri- and tetrasubstituted alkenes, including the challenging all-alkyl tetrasubstituted alkenes, undergo CAH with enantiomer ratios (er) as high as 99:1. The mild reaction conditions, i.e., ambient temperature, moderate reaction times, and the need for only a slight excess of H2, contrast those used in most state-of-the-art catalysts for related substrates.

SUBMITTER: Shoba VM

PROVIDER: S-EPMC5408738 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes.

Shoba Veronika M VM Takacs James M JM

Journal of the American Chemical Society 20170417 16

Oxime-directed catalytic asymmetric hydroboration is diverted to catalytic asymmetric hydrogenation (CAH) upon the addition of a proton source, such as MeOH, or by running the reaction under a hydrogen atmosphere. A borane (e.g., pinacolborane) is required to promote CAH. Tri- and tetrasubstituted alkenes, including the challenging all-alkyl tetrasubstituted alkenes, undergo CAH with enantiomer ratios (er) as high as 99:1. The mild reaction conditions, i.e., ambient temperature, moderate reactio ...[more]

PMID: 28394591

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