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A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres
Robert V. Hoffman1, Junhua Tao
1Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico 88003-0001.
The Journal of Organic Chemistry
|October 25, 2001
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%).