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Formation of azatitanacyclopentanes from ene-imines and a Ti(O-i-Pr)4/2i-PrMgX reagent and their synthetic reactions
Authors:Wataru Uchikawa
Affiliation:Department of Applied Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
Abstract:ω-Vinylimines reacted with a Ti(O-i-Pr)4/2i-PrMgX reagent to generate the corresponding azatitanacyclopentanes in quantitative yield, which in turn reacted with H2O, I2 and O2 to give 2-methyl-, 2-iodomethyl-, 2-hydroxymethyl-1-aminocyclic compounds, respectively. The azatitanacyclopentanes thus generated reacted with formaldehyde to afford the corresponding 2,3-annulated pyrrolidines in good yield.
Keywords:Low valent titanium   Azatitanacyclopentane   Cyclization   Ene-imine
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