Cycloadditions of Carbonyl Ylides Derived from Diazocarbonyl Compounds

摘要: [3 + 2] cycloadditions of carbonyl ylides with dipolarophiles provides a synthetically powerful way to make variety 5-membered oxacycles. One the best ways generate ylide intermediates is by transition metal-catalyzed loss nitrogen from diazocarbonyl compounds and trapping resultant metallocarbenes group. This chapter covers intra- intermolecular derived various dipolarophiles. The literature up end 2011 covered. A comprehensive discussion provided mechanism stereochemistry, regioselectivity, stereoselectivity, asymmetric cycloadditions. structural scope at diazo group, group forming ylide, dipolarophile delineated. A systematic analysis presented limitations cyclic diazocarbonyl-derived ketones, esters, amides or imides, including aromatic pyrylium isomunchnone ylides. generation acyclic aldehydes, imides their also reviewed. Finally, important applications total synthesis natural products critical comparison other methods for generation-cycloaddition are presented. Keywords: cycloaddition reaction(s); [3 + 2] reaction(S); intermolecular cycloaddition(s); intramolecular cycloaddition(s); metal catalyzed; diazo compound(s); carbonyl ylide(s); pyrylium(s); isomunchnone(s); natural product(s); asymmetric catalysis; stereochemistry; method comparisons; experimental procedures