Biomimetic Desymmetrization of a Carboxylic Acid

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https://doi.org/10.1021/jacs.7b12185
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5814305

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2018-02-05

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https://hdl.handle.net/2022/30478

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.

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Knowe, Matthew T., et al. "Biomimetic Desymmetrization of a Carboxylic Acid." Journal of the American Chemical Society, vol. 140, no. 6, pp. 1998-2001, 2018-02-05, https://doi.org/10.1021/jacs.7b12185.

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Journal of the American Chemical Society

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Faculty Open Access Articles