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Noncovalent Catalysis for Enantioselective Direct Aldol Reaction of 3‐Acetylcoumarins to Pyrazole‐4,5‐diones
Author(s) -
Ray Bidisha,
Singha Roy Soumya Jyoti,
Mukherjee Santanu
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800732
Subject(s) - chemistry , enantioselective synthesis , stereocenter , aldol reaction , bifunctional , organocatalysis , pyrazole , catalysis , amide , combinatorial chemistry , stereochemistry , organic chemistry
The first catalytic enantioselective direct aldol reaction of 3‐acetylcoumarins to pyrazole‐4,5‐diones is reported and shown to proceed through noncovalent substrate activation by a quinine‐derived bifunctional tertiary amino‐amide as the catalyst. The densely functionalized products, consisting of an oxygen‐containing quaternary stereocenter and bearing two biologically relevant heterocycles, are generally obtained in high yields with moderate to excellent enantioselectivities.