title: Completely stereocontrolled aldol reaction of chiral β-amino acids.
abstract: A general protocol to independently access stereoisomerically pure β'-hydroxy-β-amino acid derivatives that is based on dibutylboron triflate-mediated aldol reaction of suitably protected β-amino acids bearing chiral oxazolidinone auxiliary is reported. The method smoothly afforded syn-aldol (α,β'-syn) products in pure form and excellent isolated yield. Both α,β-syn and α,β-anti isomers are readily accessible solely through the choice of the oxazolidinone chirality. This method allows for the preparation of stereoisomeric β'-hydroxy-β-amino acid derivatives that were previously unreported.
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana , Večna pot 113, SI-1000 Ljubljana, Slovenia.
authors.forename: Martin
authors.initials: M
authors.lastname: Gazvoda
authors.forename: Kathrin
authors.initials: K
authors.lastname: Höferl-Prantz
authors.forename: Roland
authors.initials: R
authors.lastname: Barth
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Felzmann
authors.forename: Andrej
authors.initials: A
authors.lastname: Pevec
authors.forename: Janez
authors.initials: J
authors.lastname: Košmrlj
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D004952:Esters; C116609:3-hydroxybutanal