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A short, efficient synthesis of monofluoro ketomethylene peptide isostere core units

โœ Scribed by Robert V. Hoffman; James E. Saenz

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
194 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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.

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: A Short, Efficient
ChemInform Abstract: A Short, Efficient Synthesis of Monofluoro Ketomethylene Peptide Isostere Core Units.
โœ R. V. HOFFMAN; J. E. SAENZ ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 32 KB ๐Ÿ‘ 2 views

Title compounds of type (VII) (6 examples) are readily prepared following the 4-step sequence presented. The introduction of the fluorine substituent is best achieved using selectfluor under the optimized conditions shown.

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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).

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