Tetrahedron

Ligand effects in the rhodium (II) catalysed reactions of diazoamides and diazoimides

…, CJ Moody, SM Sheehan, JP Marino, MA Semones…

Index: Miah, Soyfur; Slawin, Alexandra M. Z.; Moody, Christopher J.; Sheehan, Scott M.; Marino Jr., Joseph P.; Semones, Mark A.; Padwa, Albert; Richards, Ian C. Tetrahedron, 1996 , vol. 52, # 7 p. 2489 - 2514

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Citation Number: 52

Abstract

A range of substituted α-diazoamides 1–8 and diazoimides 9–12 was prepared from the corresponding amines or amides. Rhodium (II) catalysed decomposition of the diazoamides resulted in attack on the aromatic ring to give oxindoles or attack on the alkyl group to give either β-lactams or cycloheptapyrrolones. The chemoselectivity of the rhodium carbenoid intermediate was dependent on the metal ligands, fluorinated carboxamides strongly ...