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Carbene‐Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products
Author(s) -
Liu Yingguo,
Majhi Pankaj Kumar,
Song Runjiang,
Mou Chengli,
Hao Lin,
Chai Huifang,
Jin Zhichao,
Chi Yonggui Robin
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201912926
Subject(s) - kinetic resolution , acylation , carbene , chemistry , catalysis , enantiomer , acetal , enantioselective synthesis , molecule , combinatorial chemistry , stereoisomerism , organic chemistry
A catalytic dynamic kinetic resolution and asymmetric acylation reaction of hydroxyphthalides is developed. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine. It also enables asymmetric modification of natural products and other functional molecules that contain acetal/ketal groups, such as corollosporine and fimbricalyxlactone C.