title: Amino acid-based synthesis of trifluoromethylalkene dipeptide isosteres by alcohol-assisted nucleophilic trifluoromethylation and organozinc-copper-mediated S(N)2' alkylation.
abstract: A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF(3)-ADI) has been developed. Starting from readily available l-phenylalanine and l-alanine, several CF(3)-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Kazuya
authors.initials: K
authors.lastname: Kobayashi
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Narumi
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis*; D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D000475:Alkenes; D000596:Amino Acids; D004151:Dipeptides; D008698:Mesylates; D009942:Organometallic Compounds; D010649:Phenylalanine; D003300:Copper; D015032:Zinc; D000409:Alanine