title: Synthesis of fluorinated pseudopeptides: metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines.
abstract: The addition reaction of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines was studied. Depending of the nature of the organometallic species (Grignard reagents or zincate complexes), we were able to control the configuration of the newly created stereogenic centers in high yields with good to high diastereomeric ratios. The chiral β-fluoro allylamines are key synthons toward the synthesis of fluorinated pseudopeptides bearing a fluoroolefin moiety as a peptide bond mimic.
authors.affiliation: UMR 6014 CNRS-C.O.B.R.A., Université et INSA de Rouen, 1 rue Tesnière, 76130 Mont Saint Aignan, France.
authors.forename: Camille
authors.initials: C
authors.lastname: Pierry
authors.forename: Dominique
authors.initials: D
authors.lastname: Cahard
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
mesh_terms: D002073:Butanes / Q000737:chemistry; D017611:Fluorine Compounds / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D002073:Butanes; D017611:Fluorine Compounds; D007097:Imines; D009942:Organometallic Compounds; D010455:Peptides; D013457:Sulfur Compounds; C046888:butane