Biomimetic Desymmetrization of a Carboxylic Acid.

Matthew T KnoweMichael W DannemanSarah SunMaren PinkJeffrey N Johnston

Published in: Journal of the American Chemical Society (2018)

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.

Keyphrases

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