Selective Reactions of Azide-Substituted α-Diazo Amides with Olefins and Alcohols Using Rhodium(II) Catalysts

Article abstract of DOI:10.1021/jo00376a057

The synthesis and addition of azide-substituted α-diazo amides such as N-(4-azidophenyl)-α-diazoacetamide and N-(4-azido-2-hydroxyphenyl)-α-diazoacetamide to olefins and alcohols using either rhodium(II) acetate or preferably rhodium(II) pivalate provided cyclopropanecarboxamides and α-alkoxy amides, respectively, without disrupting the azide functionality.These azide-bearing α-diazo amides are potentially useful in the preparation of photoaffinity cross-linking reagents for studying the mechanism of action of natural products.