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Kinetic Resolution of Oxazinones: An Organocatalytic Approach to Enantiomerically Pure β‐Amino Acids
Author(s) -
Berkessel Albrecht,
Cleemann Felix,
Mukherjee Santanu
Publication year - 2005
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.200502003
Subject(s) - thiourea , kinetic resolution , chemistry , resolution (logic) , catalysis , modular design , amino acid , organocatalysis , organic chemistry , enantioselective synthesis , combinatorial chemistry , computer science , biochemistry , programming language
A profitable split : An organocatalytic resolution converts readily available racemic oxazinones 1 into valuable enantiomerically pure β‐amino acid derivatives 2 (>99 % ee of the remaining 1 at 53 % conversion; 88 % ee of the ester 2 ). This catalytic ring‐opening reaction requires as little as 1 mol % of the modular and readily accessible thiourea organocatalyst 3 .