Organic letters

Intramolecular [3+ 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic π-systems

JM Mejía-Oneto, A Padwa

Index: Mejia-Oneto, Jose M.; Padwa, Albert Organic Letters, 2004 , vol. 6, # 19 p. 3241 - 3244

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Citation Number: 49

Abstract

Push-pull dipoles generated from the Rh (II)-catalyzed reaction of diazo imides containing tethered heteroaromatic rings undergo successful [3+ 2]-cycloaddition across the 2, 3-π- bond to provide novel pentacyclic compounds in good to excellent yields in a stereocontrolled fashion. The facility of the cycloaddition is critically dependent on conformational factors in the transition state.