title: Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters.
abstract: A zinc-ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.
authors: Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
authors: Barry M
authors: BM
authors: Trost
authors: Frédéric
authors: F
authors: Miege
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D008024:Ligands; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D004952:Esters; D008024:Ligands; D010636:Phenols; D012545:Schiff Bases; D015032:Zinc