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Rh-Catalyzed Desymmetrization of ?-Quaternary Centers by Isomerization-Hydroacylation.


ABSTRACT: We describe a Rh-catalyzed desymmetrization of all-carbon quaternary centers from ?,?-bis(allyl)aldehydes by a cascade featuring isomerization and hydroacylation. This desymmetrization competes with two other novel olefin functionalizations that are triggered by C-H bond activation, including carboacylation and bisacylation. A BIPHEP ligand promotes enantioselective formation of ?-vinylcyclopentanones. Mechanistic studies support irreversible and enantioselective olefin-isomerization followed by olefin-hydroacylation.

SUBMITTER: Park JW 

PROVIDER: S-EPMC4618402 | BioStudies | 2015-01-01

REPOSITORIES: biostudies

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