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

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概要

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• <I>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.</I>

• 社団法人 有機合成化学協会の論文

著者

• ANADA Masahiro

  Faculty of Pharmaceutical Sciences, Hokkaido University

• Hashimoto Shun-ichi

  Faculty Of Pharmaceutical Sciences Teikyo University

• IKEGAMI Shiro

  Faculty of Pharmaceutical Sciences, Teikyo University

• Ikegami Shiro

  Faculty Of Pharmaceutical Sciences Teikyo University

• Watanabe Nobuhide

  Faculty of Pharmaceutical Sciences, Hokkaido University

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

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