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Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions
Author(s) -
Znabet Anass,
Ruijter Eelco,
de Kanter Frans J. J.,
Köhler Valentin,
Helliwell Madeleine,
Turner Nicholas J.,
Orru Romano V. A.
Publication year - 2010
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.201001592
Subject(s) - desymmetrization , chemistry , ugi reaction , stereoselectivity , monoamine oxidase , combinatorial chemistry , stereochemistry , organic chemistry , enzyme , enantioselective synthesis , isocyanide , catalysis
Time and pep‐tide wait for no man : Optically pure 3,4‐disubstituted 1‐pyrrolines, generated from the corresponding meso ‐pyrrolidines by biocatalytic desymmetrization (MAO‐N=monoamine oxidase N), react with carboxylic acids and isocyanides in a highly diastereoselective Ugi‐type multicomponent reaction to give substituted prolyl peptides of high pharmaceutical relevance.