Biomimetic Desymmetrization of a Carboxylic Acid.

ABSTRACT: The enantioselective desymmetrization of carboxylic acids by chiral Brønsted base catalysis is reported, leading to bridged bicyclic lactones with up to 94% ee. Crystallographic analysis of a substrate-catalyst complex suggests an origin of stereocontrol, reminiscent of functional Brønsted bases in biological settings, and enabled reaction optimization. The products contain an all-carbon quaternary stereocenter and can be derivatized to functionalized cyclopentanes.

SUBMITTER: Knowe MT 

PROVIDER: S-EPMC5814305 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature