Cyclization cycloaddition cascades for the construction of azapolycyclic ring systems

A Padwa, WS Kissell, CK Eidell

Index: Padwa, Albert; Kissell, William S.; Eidell, Cheryl K. Canadian Journal of Chemistry, 2001 , vol. 79, # 11 p. 1681 - 1693

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Citation Number: 10

Abstract

Cyclic 2-amidofuranones were obtained from the Rh (II)-catalyzed reaction of alpha- diazoketo substituted pyrrolidine derivatives. These compounds are derived by a [1, 4]- hydrogen transfer from an initially formed carbonyl ylide dipole. Acylation of the amido- substituted furanone with pivalyl chloride provided a fused amidofuran, which underwent bimolecular Diels-Alder cycloaddition with N-phenylmaleimide. The Rh (II)-catalyzed ...