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Enantioselective Henry Reactions under Dual Lewis Acid/Amine Catalysis Using Chiral Amino Alcohol Ligands

Authors

  • Claudio Palomo Prof. Dr.,

    1. Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-015-270
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  • Mikel Oiarbide Prof. Dr.,

    1. Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-015-270
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  • Antonio Laso

    1. Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain, Fax: (+34) 943-015-270
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  • This work was financially supported by the University of the Basque Country and the Ministerio de Educación y Ciencia (MEC, Spain). A predoctoral grant to A.L. from the MEC is acknowledged.

Abstract

original image

A simple assembly of commercially available materials, namely, zinc triflate (Zn(OTf)2), a tertiary amine base (iPr2EtN), and reusable (+)-N-methylephedrine, effectively activates the Henry reaction between aldehydes and nitromethane (see scheme). The catalytic system can be used in substoichiometric quantities and leads to good yields and enantioselectivities.

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