Michael Addition of Nitroalkanes to Optically Active Acrylates Mediated by Cetyltrimethylammonium Hydroxide (CTAOH)

Roberto      Ballini; Dennis      Fiorini; Alessandro      Palmieri; Marino      Petrini

doi:10.2174/1570178043400677

Abstract

Nitroalkanes react with chiral acrylates in the presence of a catalytic amount (10% mol) of CTAOH in small amount of water as solvent. Although only modest levels of diastereoselectivity can be observed in this process, the obtained Michael adducts can be easily transformed into interesting building blocks as γ-amino acids and cyclic hydroxycarbamates.

Keywords: conjugate addition, nitroalkanes, diastereoselective reaction

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Letters in Organic Chemistry

Title: Michael Addition of Nitroalkanes to Optically Active Acrylates Mediated by Cetyltrimethylammonium Hydroxide (CTAOH)

Volume: 1 Issue: 4

Author(s): Roberto Ballini, Dennis Fiorini, Alessandro Palmieri and Marino Petrini

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Keywords: conjugate addition, nitroalkanes, diastereoselective reaction

Abstract: Nitroalkanes react with chiral acrylates in the presence of a catalytic amount (10% mol) of CTAOH in small amount of water as solvent. Although only modest levels of diastereoselectivity can be observed in this process, the obtained Michael adducts can be easily transformed into interesting building blocks as γ-amino acids and cyclic hydroxycarbamates.

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Ballini Roberto, Fiorini Dennis, Palmieri Alessandro and Petrini Marino, Michael Addition of Nitroalkanes to Optically Active Acrylates Mediated by Cetyltrimethylammonium Hydroxide (CTAOH), Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400677