title: Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate.
abstract: The enantiopure Davis' N-sulfinylimines were found to be efficient as chiral imine equivalents in the high-temperature Reformatsky-type additions with BrZnCF(2)COOEt affording an efficient approach to the enantiomerically pure alpha,alpha-difluoro-beta-amino acids. High chemical and stereochemical yields (drs > 9:1, and as high as 99:1) render this method immediately useful for preparing the target amino acids.
authors.affiliation: Institute of Bioorganic Chemistry and Petrochemistry, Ukrainian Academy of Sciences, Kiev-94, 253660, Ukraine. sorochinsky@bpci.kiev.ua
authors.forename: Alexander
authors.initials: A
authors.lastname: Sorochinsky
authors.forename: Natalia
authors.initials: N
authors.lastname: Voloshin
authors.forename: Andrey
authors.initials: A
authors.lastname: Markovsky
authors.forename: Michael
authors.initials: M
authors.lastname: Belik
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Yasuda
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.forename: Taizo
authors.initials: T
authors.lastname: Ono
authors.forename: Dmitrii O
authors.initials: DO
authors.lastname: Berbasov
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D005461:Fluorine / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
chemical_list: D000596:Amino Acids; D007097:Imines; D013452:Sulfonium Compounds; D005461:Fluorine