A simple, stel'eoc~ntrollod synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. The method is short (6 sleps) and diastereoselective (85-95% de) and enantioselective (>95% ee).
A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres
โ Scribed by Hoffman, Robert V.; Tao, Junhua
- Book ID
- 120814856
- Publisher
- American Chemical Society
- Year
- 1999
- Tongue
- English
- Weight
- 261 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0022-3263
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-~/-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and hi
A general stereo-directed synthesis of "ketomethylene" and "hydroxyethylene" dipeptide isosteres is reported. Peptides containing the amino acids, (2&%)-5-amino-4-oxo-2,8dimethyloctanoic acid (the "ketomethylene" analog of L-Leu-L-Ala), and (2&,5z)-5-amino-4-hydroxy-2,8-dimethyloctanoic acid (the "h
Monofluoro ketomethylene peptide isosteres can be prepared by a four step sequence from earboxylic acids in satisfactory overall yields (30-60%). Fluorine is introduced by electrophilic fluorination of a ~-ketoester enolate with SelectFluor TM.