Oxazoline N-Oxide Mediated [3+2] Cycloadditions: Application to a Formal Synthesis of a (+)-β-Methylcarbapenem

Abstract

[3+2] Cycloaddition between a camphor-derived oxazoline N-oxide 9 and the γ,δ-unsaturated enamino ester 11 afforded the single adduct 6. A stereoselective reduction of the enamino ester side chain allowed the control of the absolute configuration of the two additional asymmetric centres. Nitrogen