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

The asymmetric dirhodium(II)‐catalyzed intramolecular CH 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 l...

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Veröffentlicht in:Advanced synthesis & catalysis 2012-11, Vol.354 (16), p.2921-2927
Hauptverfasser: Candeias, Nuno R., Carias, Carolina, Gomes, Luis F. R., André, Vânia, Duarte, M. Teresa, Gois, Pedro M. P., Afonso, Carlos A. M.
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Sprache:eng
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Zusammenfassung:The asymmetric dirhodium(II)‐catalyzed intramolecular CH 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201200101