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N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,ß-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields. It reacts with asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines. It is used in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds.
A. Stephen K. Hashmi; Dominic Riedel; Matthias Rudolph; Frank Rominger; Thomas Oeser. Regioselective Formation of Saturated Abnormal NHC-Gold(I) Complexes by [3+2] Cycloaddition of Azomethine Ylides and Isonitrile Gold(I) Complexes. Org. Biomol. Chem.2012, 18, 3827-3830.
Ultrasound treatment with LiF in acetonitrile generates an azomethine ylide which undergoes 1,3-dipolar cycloaddition to olefins to give pyrrolidine derivatives in good yield: J. Org. Chem., 52, 235 (1987). Also found use in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds: J. Org. Chem., 66, 2526 (2001).
Gefahrenhinweise (EU): H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
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