Conversion of α-Keto Esters into β,β-Difluoro-α-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors

Melchiorre F. Parisi, Giuseppe Gattuso, Anna Notti, Françisco M. Raymo, Robert H. Abeles

Research output: Contribution to journalArticle

33 Scopus citations

Abstract

The preparation of a series of β,β-difluoro-α-keto esters and corresponding acids RCF2COCO2R′ (R = Me, Et, i-Pr, Bn, and Ph; R′ = Et and H), designed as potential inhibitors of serine proteases, is described. The standard procedure developed consists in the initial formation of an α,α-difluoro ester from an α-keto ester, followed by a simple four-step sequence involving the synthesis of hemiacetal, cyanohydrin, and α-hydroxy ester difluorinated intermediates. This method provides an easy route to β,β-difluoro-α-keto esters and corresponding acids, via "formal" insertion of a difluoromethylene group between the R substituent and the α-carbonyl group of a generic α-keto ester.

Original languageEnglish (US)
Pages (from-to)5174-5179
Number of pages6
JournalJournal of Organic Chemistry
Volume60
Issue number16
DOIs
StatePublished - Aug 1 1995
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Conversion of α-Keto Esters into β,β-Difluoro-α-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors'. Together they form a unique fingerprint.

  • Cite this