The azomethine ylide strategy for β-lactam synthesis. An evaluation of alternative pathways for azomethine ylide generation

…, SR Martel, R Wisedale, JPH Charmant…

Index: Brown, Giles A.; Martel, Sarah R.; Wisedale, Richard; Charmant, Jonathan P.H.; Hales, Neil J.; Fishwick, Colin W.G.; Gallagher, Timothy Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 11 p. 1281 - 1289

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Citation Number: 17

Abstract

Following the generation of azomethine ylide 3 from the β-lactam-based oxazolidinone 1, a series of alternative entries to this and related 1, 3-dipoles have been explored. The first approach is based on the use of monocyclic azetidinones 6–12 and 14 carrying a leaving group at C (4) and an activated (acidic) proton adjacent to the ring nitrogen, structural moieties which are both associated with 1. These monocyclic substrates show no ...