The ester enolate-imine condensation route to β-lactams

David J. Hart, Deok-Chan Ha

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Abstract

It is clear that the ester-imine condensation route to β-lactams has been highly developed over the past decade. The behaviors of a broad spectrum of enolates and azomethines have been delineated and some mechanistic features of these reactions are understood, although it is in this area where in-depth understanding is still lacking. Nonetheless, the reaction has been developed to a stage where it has been applied to the synthesis of β-lactam antibiotics as illustrated herein by partial syntheses of carbapenems. Applications to monobactam substructures have also been reported, and the use of this reaction in other areas of natural and nonnatural product synthesis can be anticipated.

Original languageEnglish
Pages (from-to)1447-1465
Number of pages19
JournalChemical Reviews
Volume89
Issue number7
Publication statusPublished - 1989 Dec 1
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

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