Login / Signup

Entry to Chiral 1,1,2,3-Tetrasubstituted Arylcyclopropanes by Pd(II)-Catalyzed Arylation via Directing Group-Mediated C(sp3)-H Activation.

Naoyuki HoshiyaMoemi KondoHayato FukudaMitsuhiro ArisawaJun'ichi UenishiSatoshi Shuto
Published in: The Journal of organic chemistry (2017)
Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd(II)-catalyzed arylation via directing group-mediated C(sp3)-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • room temperature
  • solid phase extraction