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Aminocatalyzed reactions of aldehydes with chiral nitroalkenes

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Chiral nitroalkenes are used for the first time in Michael additions of aldehydes, catalyzed by pyrrolidine derivatives. They yield the same major stereoisomer with either (S)-proline or (R)-proline, but this asymmetric induction does not overcome the effect of sterically more congested catalysts. Nitrocyclobutane intermediates are often formed, which are more stable than those from (E)-1-nitro-2-phenylethene. The cyclobutanes and final products were characterized by 2D NMR and chemical correlations

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CASCALES JIMÉNEZ, Victor, et al. Aminocatalyzed reactions of aldehydes with chiral nitroalkenes. Organic Letters. 2021. Vol. 23, num. 3, pags. 651-655. ISSN 1523-7060. [consulted: 23 of May of 2026]. Available at: https://hdl.handle.net/2445/186040

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