Journal of the American Chemical Society p. 1998 - 2001 (2018)
Update date:2022-08-03
Topics:
Knowe, Matthew T.
Danneman, Michael W.
Sun, Sarah
Pink, Maren
Johnston, Jeffrey N.
The enantioselective desymmetrization of carboxylic acids by chiral Br?nsted 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 Br?nsted 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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