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Synlett 2012(5): 765-767  
DOI: 10.1055/s-0031-1290598
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Investigation of Additive Effects in Enantioselective Copper-Catalysed C-H Insertion and Aromatic Addition Reactions of α-Diazocarbonyl Compounds

Catherine N. Slatterya, Leslie-Ann Clarkea, Shane O’Neilla, Aoife Ringa, Alan Forda, Anita R. Maguire*b
a Department of Chemistry and Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
b Department of Chemistry, School of Pharmacy and Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
Fax: +353(21)4274097; e-Mail: a.maguire@ucc.ie;
Further Information

Publication History

Received 4 November 2011
Publication Date:
28 February 2012 (online)

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Abstract

Significant enhancements in enantioselectivities and reaction efficiencies in asymmetric copper-catalysed C-H insertion and aromatic addition reactions of α-diazocarbonyl compounds in the presence of various group I salts are reported. For the first time in carbenoid chemistry, evidence for the critical role of the metal cation is described.

Key words

diazocarbonyl - copper catalysis - C-H insertion - ­Buchner reaction - bis(oxazoline) ligands

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Presence of NaCl confirmed by PXRD analysis (see Supporting Information for details).