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, Francisco Raymo, Robert H. Abeles

Research output: Contribution to journalArticle

32 Citations (Scopus)

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
Pages (from-to)5174-5179
Number of pages6
JournalThe Journal of Organic Chemistry
Volume60
Issue number16
StatePublished - Dec 1 1995
Externally publishedYes

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Serine Proteinase Inhibitors
Esters
Acids

ASJC Scopus subject areas

  • Organic Chemistry

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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. / Parisi, Melchiorre F.; Gattuso, Giuseppe; Notti, Anna; Raymo, Francisco; Abeles, Robert H.

In: The Journal of Organic Chemistry, Vol. 60, No. 16, 01.12.1995, p. 5174-5179.

Research output: Contribution to journalArticle

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