Letters in Organic Chemistry

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

DOI: 10.2174/1570178043400677

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

Page: [335 - 339] Pages: 5

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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