Synthesis 2012; 44(8): 1178-1182
DOI: 10.1055/s-0031-1290590
special topic
© Georg Thieme Verlag Stuttgart · New York

Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

Arantxa Rodríguez
Department of Chemical & Biological Sciences, Queensgate, Huddersfield, HD1 3DH, UK, Fax: +44(1484)472182   Email: w.j.moran@hud.ac.uk
,
Wesley J. Moran*
Department of Chemical & Biological Sciences, Queensgate, Huddersfield, HD1 3DH, UK, Fax: +44(1484)472182   Email: w.j.moran@hud.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 09 February 2012

Accepted after revision: 24 February 2012

Publication Date:
16 March 2012 (online)


Abstract

Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

 
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