A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres.
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%).
Hoffman
Robert V.
RV
Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico 88003-0001.
Tao
Junhua
J