Intramolecular cyclopropanation reaction of furanyl diazo ketones

A Padwa, TJ Wisnieff, EJ Walsh

Index: Padwa, Albert; Wisnieff, Thomas J.; Walsh, Edward J. Journal of Organic Chemistry, 1989 ,  vol. 54,  # 2  p. 299 - 308

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Citation Number: 44

Abstract

a-Diazo ketones derived from furanyl-and benzofuranylpropionic acids were prepared, and their rhodium (I1) acetate catalyzed behavior was studied. The results are consistent with a mechanism in which the key step involves addition of a keto carbenoid intermediate on to the furanyl*-bond followed by an electrocyclic ring-opening reaction. In the case of the benzo-substituted furanyl system, the suspected bicyclic intermediate was isolated in high ...