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Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.

ABSTRACT: Alkenes are desirable and highly versatile starting materials for organic transformations, and well-known substrates for palladium catalysis. Typically, these reactions result in the formation of a new alkene product via ?-hydride elimination. In contrast to this scenario, our laboratory has been involved in the development of alkene hydro- and difunctionalization reactions, where ?-hydride elimination can be controlled. We report herein the development of an asymmetric palladium-catalyzed hydroarylation, which yields diarylmethine products in up to 75% ee. Interestingly, a linear free energy relationship is observed between the steric bulk of the ligand within a certain range and the enantiomeric excess of the reaction.

SUBMITTER: Podhajsky SM

PROVIDER: S-EPMC3129978 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.

Podhajsky Susanne M SM Iwai Yasumasa Y Cook-Sneathen Amanda A Sigman Matthew S MS

Tetrahedron 20110601 24

Alkenes are desirable and highly versatile starting materials for organic transformations, and well-known substrates for palladium catalysis. Typically, these reactions result in the formation of a new alkene product via β-hydride elimination. In contrast to this scenario, our laboratory has been involved in the development of alkene hydro- and difunctionalization reactions, where β-hydride elimination can be controlled. We report herein the development of an asymmetric palladium-catalyzed hydro ...[more]

PMID: 21743752

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