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Hydrogen‐Bonding Assisted Catalytic Kinetic Resolution of Acyclic β‐Hydroxy Amides
Author(s) -
Porey Arka,
Mondal Bhaskar Deb,
Guin Joyram
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202015004
Subject(s) - kinetic resolution , enantioselective synthesis , chemistry , acylation , selectivity , catalysis , diastereomer , hydrogen bond , amine gas treating , carbene , combinatorial chemistry , organic chemistry , molecule
Enantioenriched acyclic α‐substituted β‐hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N ‐heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.