Enantioselective Si-H insertion of methyl phenyldiazoacetate catalyzed by dirhodium(II) carboxylates incorporating N-phthaloyl-(S)-amino acids as chiral bridging ligands

Enantioselective insertion reactions of methyl phenyldiazoacetate into the Si-H bond of silanes were effected by employing dirhodium(II) carboxylates incorporating N-phthaloyl-(S)-amino acids as chiral bridging ligands. The use of dirhodium(II) tetrakis [N-phthaloyl-(S) -phenylalaninate] as a catalyst produced methyl (2S)-(dimethylphenylsilyl)phenylacetate in 74% ee, whereas catalysis with dirhodium(II) tetrakis[N-phthaloyl-(S)-phenylglycinate] afforded its enantiomer in 72% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.