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L ‐Amino Acid Amides via Dynamic Kinetic Resolution
Author(s) -
Tessaro Davide,
Cerioli Lorenzo,
Servi Stefano,
Viani Fiorenza,
D'Arrigo Paola
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100389
Subject(s) - chemistry , racemization , kinetic resolution , aminolysis , enantiomer , amino acid , catalysis , stereochemistry , enantioselective synthesis , amide , organic chemistry , enantiomeric excess , biochemistry
Racemic natural and non‐natural N ‐Boc‐amino acid thioesters undergo enzyme‐catalyzed ammoniolysis and aminolysis with concomitant base‐catalyzed racemization of the non‐transformed D ‐enantiomer with the formation of the corresponding L ‐amides in good yields and excellent enantiomeric purity all above 98% ee . This is the first example of a dynamic kinetic resolution of amino acid derivatives with amides formation.