Synfacts 2007(7): 0771-0771  
DOI: 10.1055/s-2007-968694
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

α-Aminoxylation of Aldehydes and Ketones with a Polymer-Supported Organocatalyst

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
D. Font, A. Bastero, S. Sayalero, C. Jimeno, M. A. Pericàs*
Institute of Chemical Research of Catalonia (ICIQ), Tarragona and Universitat de Barcelona, Spain
Further Information

Publication History

Publication Date:
22 June 2007 (online)

Significance

The catalytic enantioselective α-aminoxylation of aldehydes and ketones by using polymer-supported organocatalyst 1 derived from trans-4-hydroxyproline was described. The reaction of aldehydes 2 with nitrosobenzene in the presence of catalyst 1 gave the aminoxylated products 3 which were readily transformed to the corresponding aminoxylated primary alcohols 4 in 35-86% yield and 96-99% ee (eq. 1). α-Aminoxylation of ketones 5 was also carried out in the presence of catalyst 1 to give the corresponding compounds 6 in 49-74% yield with 97-99% ee (eq. 2).