Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles

Authors

  • Andrea Baschieri,

    1. Dipartimento di Chimica Organica “A. Mangini”, Facoltà di Chimica Industriale, Università di Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • Luca Bernardi Dr.,

    1. Dipartimento di Chimica Organica “A. Mangini”, Facoltà di Chimica Industriale, Università di Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • Alfredo Ricci Prof.,

    1. Dipartimento di Chimica Organica “A. Mangini”, Facoltà di Chimica Industriale, Università di Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • Surisetti Suresh Dr.,

    1. Centre for Synthesis and Chemical Biology (CSCB), Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2 (Ireland), Fax: (+353) 1-402-2168
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  • Mauro F. A. Adamo Dr.

    1. Centre for Synthesis and Chemical Biology (CSCB), Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2 (Ireland), Fax: (+353) 1-402-2168
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  • We acknowledge financial support from “Stereoselezione in Sintesi Organica Metodologie e Applicazioni” 2007. Financial support by the Merck-ADP grant 2007, the Health Research Board (HRB), Science Foundation Ireland (SFI), and Enterprise Ireland is also gratefully recognized.

Abstract

original image

Nitro versus nitro: 4-Nitro-5-styrylisoxazoles were used as masked α,β-unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4-nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol % of a readily prepared phase-transfer catalyst at room temperature with remarkable diastereo- and enantioselectivity (see scheme).

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