Synfacts 2011(5): 0506-0506  
DOI: 10.1055/s-0030-1259874
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-Catalyzed Allylic Hydroxylation

Contributor(s): Hisashi Yamamoto, Jiajing Tan
M. Gärtner, S. Mader, K. Seehafer, G. Helmchen*
Ruprecht-Karls-Universität Heidelberg, Germany
Further Information

Publication History

Publication Date:
15 April 2011 (online)

Significance

Chiral phosphoramidite ligands have been successfully employed in asymmetric allylic alkylation and amination reactions; however, the allylic substitution reaction with O-nucleophiles is less developed. In this paper, the authors developed a novel, air- and moisture-stable iridium/chiral phosphoramidite complex, which nicely catalyzes the direct enantioselective allylic hydro­xylation to prepare highly enantioenriched branched allylic alcohol products directly. This work is an important addition to previously reported enantioselective allylic hydroxylation (I. Lyothier, C. Defieber, E. M. Carreira Angew. Chem. Int. Ed. 2006, 45, 6204).