Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction. Academic Article uri icon

abstract

  • Pre-equilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to afford substituted lactams stereoselectively. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate leading toward pinnaic acid.

published proceedings

  • J Am Chem Soc

altmetric score

  • 6.664

author list (cited authors)

  • Liu, R., Gutierrez, O., Tantillo, D. J., & Aub, J.

citation count

  • 62

complete list of authors

  • Liu, Ruzhang||Gutierrez, Osvaldo||Tantillo, Dean J||AubĂ©, Jeffrey

publication date

  • January 2012