title: Enantiopure trifluoromethylated β(3,3)-amino acids: synthesis by asymmetric Reformatsky reaction with stable analogues of trifluoromethyl N-tert-butanesulfinylketoimines and incorporation into α/β-peptides.
abstract: Addition of a Reformatsky reagent to α-aryl(alkyl) α-trifluoromethyl N-tert-butanesulfinyl hemiaminals, bench-stable surrogates of trifluoromethyl ketoimines, provided β-alkyl(aryl) β-trifluoromethyl β-amino acids derivatives in good yields and high diastereoselectivities. The N-tert-butanesulfinyl β(3,3)-amino esters were further utilized as versatile intermediates for the elaboration of heterodi- and -tripeptides.
authors.affiliation: Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France. fabienne.grellepois@univ-reims.fr
authors.forename: Fabienne
authors.initials: F
authors.lastname: Grellepois
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D004952:Esters; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002073:Butanes; D004952:Esters; D007097:Imines; D007202:Indicators and Reagents; D009842:Oligopeptides; D010455:Peptides; D013449:Sulfonamides; C511422:tert-butanesulfinamide