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Wiley, Advanced Synthesis & Catalysis, 16(354), p. 2921-2927, 2012

DOI: 10.1002/adsc.201200101

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Asymmetric Intramolecular CH Insertion of α‐Diazoacetamides in Water by Dirhodium(II) Catalysts Derived from Natural Amino Acids

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This paper is available in a repository.

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Abstract

The asymmetric dirhodium(II)-catalyzed intramolecular CH insertion of α-diazo acetamides in water is described for the first time. The use of natural α-amino acids as chiral ligands allowed the preparation of novel dirhodium(II) homochiral complexes by a simple procedure consisting of the in situ ligand exchange starting from dirhodium tetraacetate. The catalytic system was further reused up to 7 cycles and β-lactams were obtained in good yields and enantiomeric excess.