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Asymmetric Intramolecular CH Insertion of α‐Diazoacetamides in Water by Dirhodium(II) Catalysts Derived from Natural Amino Acids
Author(s) -
Candeias Nuno R.,
Carias Carolina,
Gomes Luis F. R.,
André Vânia,
Duarte M. Teresa,
Gois Pedro M. P.,
Afonso Carlos A. M.
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200101
Subject(s) - chemistry , intramolecular force , diazo , catalysis , enantiomer , ligand (biochemistry) , stereochemistry , amino acid , enantiomeric excess , medicinal chemistry , insertion reaction , enantioselective synthesis , organic chemistry , receptor , biochemistry
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.