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Synfacts 2010(11): 1259-1259
DOI: 10.1055/s-0030-1258797
DOI: 10.1055/s-0030-1258797
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereospecific Substitution of Allylic Alcohols
M. Roggen, E. M. Carreira*
ETH Zürich, Switzerland
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)
Significance
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).