1.
J Am Chem Soc
; 140(6): 1998-2001, 2018 02 14.
Artigo
em Inglês
| MEDLINE
| ID: mdl-29400455
RESUMO
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.