Kinetic Resolution of Oxazinones: An Organocatalytic Approach to Enantiomerically Pure β-Amino Acids

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 m...

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Veröffentlicht in:	Angewandte Chemie International Edition 2005-12, Vol.44 (45), p.7466-7469
Hauptverfasser:	Berkessel, Albrecht, Cleemann, Felix, Mukherjee, Santanu
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino Acids - chemical synthesis Amino Acids - chemistry Amino Acids - isolation & purification beta amino acids Catalysis kinetic resolution Kinetics Molecular Structure organocatalysis Oxazines - chemical synthesis Oxazines - chemistry oxazinones Stereoisomerism thiourea
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Zusammenfassung:	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.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200502003