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Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

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Details

Original languageEnglish
Pages (from-to)211-240
Number of pages30
JournalGreen Chemistry Letters and Reviews
Volume5
Issue number2
DOIs
Publication statusPublished - 2012
Publication typeA1 Journal article-refereed

Abstract

In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.

Keywords

  • diazoacetamides, C-H insertion, dirhodium(II), lactams, scCO(2), ASYMMETRIC CYCLOPROPANATION, ALPHA-DIAZOACETAMIDES, HOMOGENEOUS CATALYSIS, SUPERCRITICAL FLUIDS, CARBOXYLATES, ENANTIOSELECTIVITY, TRANSFORMATIONS, IMMOBILIZATION, ACTIVATION, STRATEGY

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