ChemInform Abstract: A Tunable Route for the Synthesis of Azomethine Imines and β‐Aminocarbonyl Compounds from Alkenes.

Abstract

A Tunable Route for the Synthesis of Azomethine Imines and β-Aminocarbonyl Compounds from Alkenes. -This method allows for modular preparation of stable, crystalline azomethines from simple alkenes and hydrazones. DTF calculations support a concerted alkene aminomethylation mechanism via an imino-isocyanate intermediate. The fluorenone-derived hydrazone (Id) shows high reactivity to different alkene classes and allows for mild transformation of the dipole products, e.g. into β-aminoamides (VI). -(CLAVETTE, C.; GAN, W.; BONGERS, A.; MARKIEWICZ, T.; TODERIAN, A. B.; GORELSKY, S. I.; BEAUCHEMIN*, A. M.; J. Am. Chem. Soc. 134 (2012) 39, 16111-16114, http://dx.doi.org/10.1021/ja305491t ; Cent. Catal. Res. Innov., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.; Eng.) -Nuesgen 14-133