Lewis Acid Catalyzed Asymmetric Cycloadditions of Nitrones: α′??Hydroxy Enones as Efficient Reaction Partners

C Palomo, M Oiarbide, E Arceo…

Index: Palomo, Claudio; Oiarbide, Mikel; Arceo, Elena; Garcia, Jesus M.; Lopez, Rosa; Gonzalez, Alberto; Linden, Anthony Angewandte Chemie - International Edition, 2005 , vol. 44, # 38 p. 6187 - 6190

Full Text: HTML

Citation Number: 53

Abstract

The 1, 3-dipolar cycloaddition of nitrones to alkenes [1] is an atom-economic method for the construction of isoxazolidines, which are important precursors of, for example, alkaloids, amino acids, β-lactams, and amino sugars.[2] Typically, an electron-deficient alkene is involved, with the interaction between the LUMO of the alkene and the HOMO of the nitrone being the determinant for the relative orientation of the reactants. However, steric factors ...