Stereocontrol in asymmetric S(E)' reactions of -substituted ,-unsaturated aldehydes. Academic Article uri icon

abstract

  • Asymmetric SE' reactions of (E)- and (Z)--substituted-,-unsaturated aldehydes have been studied for the stereocontrolled preparation of nonracemic alcohols. Mild exchange reactions of allylic stannanes provide access to chiral 1,3-bis(tolylsulfonyl)-4,5-diphenyl-1,3-diaza-2-borolidines. These reagents display reactivity with the -substituted ,-unsaturated aldehydes, which is characterized by matched and mismatched elements of stereocontrol. Computational analysis (using density functional theory) provides valuable insights to guide reaction development.

published proceedings

  • Org Lett

author list (cited authors)

  • Williams, D. R., Atwater, B. A., Bawel, S. A., Ke, P., Gutierrez, O., & Tantillo, D. J.

complete list of authors

  • Williams, David R||Atwater, Bruce A||Bawel, Seth A||Ke, Pucheng||Gutierrez, Osvaldo||Tantillo, Dean J

publication date

  • January 2014