4.4 Article

Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides

Journal

TETRAHEDRON
Volume 60, Issue 35, Pages 7629-7636

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.05.117

Keywords

allenamides; Diels-Alder; cycloaddition; inverse demand; l-azadiene; aza-glycoside

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An inverse electron-demand aza-[4+2] cycloaddition reaction of allenamides with 1-azadiene is described here. Effects of solvents on diastereoselectivity along with synthetic scopes and mechanistic insights are illustrated. Despite some synthetic limitations, this aza-[4+2] cycloaddition does provide a useful template for the synthesis of aza-glycoside related heterocycles. (C) 2004 Elsevier Ltd. All rights reserved.

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