CYCLOADDITIONS OF CARBONYL YLIDES DERIVED FROM DIAZOCARBONYL COMPOUNDS

摘要

Metal-catalyzed decomposition of diazo compounds 1 lead to transient met-allocarbenes 2, which can generate carbonyl ylide intermediates 3 by interaction with carbonyl systems. The carbonyl ylide intermediates 3 subsequently undergo cycloaddition if suitable dipolarophiles (A=B) are present (Scheme 1). Such a catalyzed cascade process can rapidly generate molecular complexity associated with the creation of 5-membered oxacycles 4 from readily available starting materials, and thus constitutes a useful transformation in organic synthesis. This chapter covers the metal-catalyzed intra- and intermolecular cycloadditions of carbonyl ylides derived from diazocarbonyl compounds with various dipolarophiles. The literature up to the end of 2011 is covered.