title: Diastereoselective synthesis of aliphatic α,α-difluoro-β3-amino esters via a sonocatalyzed Reformatsky reaction.
abstract: (R)-2-Phenylglycine ethyl ester was found to be a cheap and effective auxiliary for the preparation of aliphatic α,α-difluoro-β(3)-amino esters via a Reformatsky reaction performed under sonication conditions. The products were obtained in good to high yield and ≥96:4 dr, thus providing a new stereoselective route to this under-represented class of compounds. A facile one-pot removal of the phenylglycine moiety and concomitant Boc protection subsequently afforded the corresponding Boc-protected β(3)-amino esters in excellent yield.
authors: School of Chemical and Physical Sciences, Flinders University , SA 5042, Australia.
authors: Taryn L
authors: TL
authors: March
authors: Martin R
authors: MR
authors: Johnston
authors: Peter J
authors: PJ
authors: Duggan
mesh_terms: D000586:Amination; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004952:Esters; D005461:Fluorine