One-Pot Synthesis of N-tert-Butylsulfinylimines and Homoallylamine Derivatives from Epoxides

The reaction of epoxides with tert-butanesulfinamide in the presence of a Lewis acid, such as erbium triflate or boron trifluoride–diethyl ether, in THF as solvent, under microwave or thermal activation, produces N-tert-butylsulfinylimines in reasonable yields. Aromatic and gem-disubstituted and trisubstituted alkyl epoxides performed better than mono-alkyl-substituted compounds. After imine formation, a subsequent indium-promoted allylation can be carried out in the same reaction flask in a single synthetic operation leading to homoallylamine derivatives with generally high yields.The authors are grateful for continued financial support from the Spanish Ministerio de Ciencia e Innovación (MCINN) (projects CONSOLIDER INGENIO 2010-CDS2007-00006, CTQ2011-24165), the Ministerio de Economía y Competitividad (MINECO) (project CTQ2014-53695-P, CTQ2014-51912-REDC), Fondos Europeos para el Desarrollo Regional (FEDER), the Generalitat Valenciana (PROMETEO 2009/039, PROMETEOII 2014/017), and the University of Alicante, Spain