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Andrea Baschieri, Luca Bernardi, Alfredo Ricci, Surisetti Suresh and Mauro F. A. Adamo Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles Angewandte Chemie International Edition 48

Version of Record online: 4 NOV 2009 | DOI: 10.1002/anie.200905018

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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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