Regioselective De Novo Synthesis of Cyanohydroxypyridines with a Concerted Cycloaddition Mechanism
Journal of the American Chemical Society2008Vol. 130(40), pp. 13219–13221
Citations Over TimeTop 12% of 2008 papers
Jin‐Yong Lu, John A. Keith, Wei‐Zheng Shen, Markus Schürmann, Hans Preut, Timo Jacob, Hans‐Dieter Arndt
Abstract
An efficient cycloaddition reaction of 1-alkoxy-1-azadienes with alpha,alpha-dicyanoalkenes is described, which gives facile access to highly substituted 3-hydroxypyridines in very good yields and with complete regiocontrol and chemoselectivity. The reaction path was investigated in detail by quantum mechanics calculations, reporting that a concerted cycloaddition mechanism and thermodynamic control synergistically contribute to the observed selectivity.
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