An Entry to the Carbapenem Antibiotic Scaffold via the Asymmetric Kinugasa Reaction

Abstract

The copper(I)-mediated reaction between five-membered cyclic nitrones and terminal acetylenes, leading to the assembly of the basic skeleton of carbapenem antibiotics is described. The diastereoselectivity of this cycloaddition–rearrangement cascade, a process known as the Kinugasa reaction, with respect to the structure and configuration of both substrates, as well as the reaction conditions, are discussed. Application of the described methodology to sugar-derived nitrones offers an attractive entry toward thienamycin and related compounds.

Key words

β-lactams - Kinugasa reaction - carbapenem antibiotics - nitrones - acetylenes

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