Stereospecific Substitution of Allylic Alcohols

Abstract

The authors disclose a stereo­specific allylic amination of optically active allylic alcohols using an iridium phosphoramidite catalyst and sulfamic acid as ammonia equivalent. An active iridium phosphoramidite complex is also isolated and characterized. Few examples of addition of free ammonia to primary allylic alcohols exist, but high ammonia equivalents and dilution are necessary to prevent overalkylation (T. Nagano, S. Kobayashi J. Am. Chem. Soc. 2009, 131, 4200; M. J. Pouy, L. M. Stanley, J. F. Hartwig J. Am. Chem. Soc. 2009, 131, 11312).