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The full potential of rhodium (II) -catalyzed intramolecular C-H insertion reactions of α-diazo carbonyl compounds as a powerful tool for the construction of both carbocycles and heterocycles has been developed by variation of the bridging ligands of the dirhodium (II) catalysts : (1) Dirhodium (II) tetrakis (triphenylacetate) featured by the steric bulk of the bridging ligands on the rhodium has been demonstrated to exhibit an exceptionally high order of selectivity for C-H insertion into methylene over methine on a cycloalkane ring as well as for aromatic substitution over aliphatic C-H insertion. (2) Dirhodium (II) complexes incorporating N-phthaloyl- (S) -amino acids as bridging ligands have proven to be the chiral catalysts of choice for allowing high levels of differentiation of enantiotopic methylene C-H bonds and enantiotopic benzene rings, affording optically active cyclopentanone, 2-azetidinone, and 2-indanone derivatives in up to 80%, 96%, and 98% ee, respectively.

Site- and Enantiocontrol in Intramolecular C-H Insertion Reactions of .ALPHA.-Diazo Carbonyl Compounds Catalyzed by Dirhodium(II) Carboxylates.