title: A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres.
abstract: A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. N-Tritylated ketomethylene dipeptide isosteres, prepared from N-tritylated amino acids, are converted to their Z-TMS enol ethers and fluorinated with Selectfluor. There is cooperative stereocontrol between the N-tritylamine group and the alkyl group at C-2. The method is short (six steps), diastereoselective (85 --> 95%), and enantioselective (>95%).
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico 88003-0001.
authors.forename: Robert V.
authors.initials: RV
authors.lastname: Hoffman
authors.forename: Junhua
authors.initials: J
authors.lastname: Tao