Biomimetic Desymmetrization of a Carboxylic Acid

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dc.contributor.authorKnowe, Matthew T.
dc.contributor.authorDanneman, Michael W.
dc.contributor.authorSun, Sarah
dc.contributor.authorPink, Maren
dc.contributor.authorJohnston, Jeffrey N.
dc.date.accessioned2025-02-20T16:00:10Z
dc.date.available2025-02-20T16:00:10Z
dc.date.issued2018-02-05
dc.description.abstractThe 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.
dc.identifier.citationKnowe, 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.
dc.identifier.otherBRITE 3508
dc.identifier.urihttps://hdl.handle.net/2022/30478
dc.language.isoen
dc.relation.isversionofhttps://doi.org/10.1021/jacs.7b12185
dc.relation.isversionofhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5814305
dc.relation.journalJournal of the American Chemical Society
dc.titleBiomimetic Desymmetrization of a Carboxylic Acid

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