Synthesis of vicinal dimethyl chirons by asymmetric hydrogenation of trisubstituted alkenes. Academic Article uri icon


  • Roche ester derivatives were converted to trisubstituted alkenes with allylic chiral centers. Hydrogenation of these substrates with chiral analogues of Crabtree's catalyst, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst controlled. However, the peripheral functionalities and protecting groups had significant effects and could be adjusted to give high stereoselectivities. The upshot of this work is that alpha,omega-functionalized chirons to introduce 1,2-dimethyl functionalities into acyclic chains have been developed.

published proceedings

  • J Am Chem Soc

altmetric score

  • 3

author list (cited authors)

  • Zhao, J., & Burgess, K.

citation count

  • 53

complete list of authors

  • Zhao, Jian||Burgess, Kevin

publication date

  • September 2009