New synthesis of. beta.-lactams based on nitrone cycloaddition to nitroalkenes

A Padwa, KF Koehler, A Rodriguez

Index: Padwa, Albert; Koehler, Konrad F.; Rodriguez, Augusto Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 282 - 288

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Citation Number: 46

Abstract

photostationary state ratio of 1: l. Trans p-lactam 3 was smoothly converted to the thermodynamically more stable cis isomer 2 on being heated in methanol with a trace of base. The stereochemistry of the cis and trans P-lactam rings can readily be assigned on the basis of the vicinal coupling constant (JciB= 5.5-6.0 Hz vs. JtrmB= 2.5-3.0