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The Direct Catalytic Enantioselective Synthesis of Protected Aryl β‐Hydroxy‐α‐Amino Acids
Author(s) -
Willis Michael C.,
Cutting Gary A.,
Piccio Vincent J.D.,
Durbin Matthew J.,
John Matthew P.
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.200462125
Subject(s) - enantioselective synthesis , aryl , oxazoline , chemistry , catalysis , ligand (biochemistry) , perchlorate , reagent , amino acid , pyridine , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , ion , alkyl , receptor
The combination of three reagents—a tridentate pybox ligand (pybox=pyridine bis(oxazoline)), magnesium perchlorate, and Hünig base ( i Pr 2 EtN)—allows the catalytic generation of a chiral glycine enolate from 1 that undergoes highly enantioselective addition to a range of aryl aldehydes 2 . The protected aryl β‐hydroxy‐α‐amino acid products obtained include a protected version of one of the aryl serine units present in the glycopeptide antibiotic vancomycin.