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Asymmetric Synthesis of γ-Nitroesters by an Organocatalytic One-Pot Strategy

Kim L. Jensen, Pernille H. Poulsen, Bjarke S. Donslund, Fabio Morana and Karl Anker Jørgensen*

*Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Email: kajchem.au.dk

K. L. Jensen, P. H. Poulsen, B. S. Donslund, F. Morana, K. A. Jørgensen, Org. Lett., 2012, 14, 1516-1519.

DOI: 10.1021/ol3002514 (free Supporting Information)



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Abstract

An enantioselective synthesis of γ-nitroesters by a one-pot asymmetric Michael addition/oxidative esterification of α,β-unsaturated aldehydes is based on an enantioselective organocatalytic nitroalkane addition followed by an N-bromosuccinimide-based oxidation. The γ-nitroesters are obtained in good yields and enantioselectivities, and the method provides an attractive entry to optically active γ-aminoesters, 2-piperidones, and 2-pyrrolidones.

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Key Words

Nitro Compounds, Oxidative Esterification, Organocatalysis


ID: J54-Y2012-0800