Kinetic Resolution of Oxazinones: An Organocatalytic Approach to Enantiomerically Pure β‐Amino Acids | Zendy

Berkessel Albrecht | Zendy; Cleemann Felix | Zendy; Mukherjee Santanu | Zendy

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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 .

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