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Synlett 2003(12): 1915-1918  
DOI: 10.1055/s-2003-41479
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© Georg Thieme Verlag Stuttgart · New York

Formation of Optically Active Functionalized β-Hydroxy Nitrones Using a Proline Catalyzed Aldol Reaction of Aldehydes with Carbonyl Compounds and Hydroxylamines

Anders Bøgevig, Thomas B. Poulsen, Wei Zhuang, Karl Anker Jørgensen*
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark
e-Mail: kaj@chem.au.dk;
Further Information

Publication History

Received 2 June 2003
Publication Date:
19 September 2003 (online)

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Abstract

The formation of optically active nitrones from a l-prolin­e catalyzed aldol reaction of aldehydes with activated carbony­l compounds and an in situ reaction with hydroxylamines is presente­d. The reaction gives optically active N-alkyl-C-β-hydrox­y-nitrones in high yield and with up to 96% ee.

Keywords

asymmetric catalysis - nitrones - carbonyl compounds - hydroxylamines - l-proline

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