title: Direct synthesis of β-hydroxy-α-amino acids via diastereoselective decarboxylative aldol reaction.
abstract: A straightforward metal-free synthesis of anti-β-hydroxy-α-amino acids is described. The organic base-mediated decarboxylative aldol reaction of cheap, readily available α-amidohemimalonates with various aldehydes afforded under very mild conditions anti-β-hydroxy-α-amido esters in high yields and complete diastereoselectivity. Simple one-pot subsequent transformations enabled the corresponding anti-β-hydroxy-α-amino acids or in a few examples their syn diastereomers to be obtained directly using epimerization conditions.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, ENSICAEN-Université de Caen, CNRS, Institut Normand de Chimie Moléculaire, Médicinal et Macromoléculaire (INC3M) , 6, Boulevard du Maréchal Juin, 14050 Caen, France.
authors.forename: Yuttapong
authors.initials: Y
authors.lastname: Singjunla
authors.forename: Jérôme
authors.initials: J
authors.lastname: Baudoux
authors.forename: Jacques
authors.initials: J
authors.lastname: Rouden
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D004952:Esters