Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters

A direct strategy to obtain N-acyl amino acid oxime esters has been developed through the dynamic kinetic resolution of azlactones with oximes. In the presence of a chiral bisguanidinium salt catalyst, a variety of chiral N-acyl amino acid oxime esters were generated in excellent enantiomeric excess...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (80), p.14897-14900
Main Authors: Yu, Kunru, Liu, Xiaohua, Lin, Xiaobin, Lin, Lili, Feng, Xiaoming
Format: Article
Language:English
Subjects:
Amino acids
Amino Acids - chemistry
Catalysis
Construction
Dynamics
Esters
Kinetics
Lactones - chemistry
Oximes
Oximes - chemistry
Reaction kinetics
Stereoisomerism
Strategy
Synthesis
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Summary:A direct strategy to obtain N-acyl amino acid oxime esters has been developed through the dynamic kinetic resolution of azlactones with oximes. In the presence of a chiral bisguanidinium salt catalyst, a variety of chiral N-acyl amino acid oxime esters were generated in excellent enantiomeric excesses (up to 97%) and high yields (up to 99%). The active oxime esters could be used in dipeptide synthesis.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc05534b