title: Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides.
abstract: Addition of anions derived from dialkyl methylphosphonates to (Ss)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine afforded (Ss,R) addition adducts in moderate to good yield (53-75%) with excellent diastereoselectivity (94-95% de). After selective removal of the N-sulfinyl group, dipeptides containing enantiomerically pure diethyl 2-amino-3,3,3-trifluoropropylphosphonate were synthesized to investigate the influence of the trifluoromethyl substituent on N-terminal coupling.
authors.affiliation: Institute of Bioorganic Chemistry & Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanskaya, Kiev, Ukraine.
authors.forename: Kostiantyn V
authors.initials: KV
authors.lastname: Turcheniuk
authors.forename: Kateryna O
authors.initials: KO
authors.lastname: Poliashko
authors.forename: Valery P
authors.initials: VP
authors.lastname: Kukhar
authors.forename: Alexander B
authors.initials: AB
authors.lastname: Rozhenko
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.forename: Alexander E
authors.initials: AE
authors.lastname: Sorochinsky
mesh_terms: D060326:Chemistry Techniques, Synthetic; D004151:Dipeptides / Q000737:chemistry*; D008745:Methylation; D063088:Phosphoramides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004151:Dipeptides; D063088:Phosphoramides