Through-bond/through-space anion relay chemistry exploiting vinylepoxides as bifunctional linchpins. Academic Article uri icon


  • The development of new bifunctional linchpins that permit the union of diverse building blocks is essential for the synthetic utility of anion relay chemistry (ARC). The design, synthesis, and validation of three vinylepoxide linchpins for through-bond/through-space ARC are now reported. For negative charge migration, this class of bifunctional linchpins employs initial through-bond ARC by an SN 2' reaction, followed by through-space ARC exploiting a 1,4-Brook rearrangement. The trans-disubstituted vinylepoxide linchpin yields a mixture of E/Zisomers, whereas the cis-disubstituted and the trans-trisubstituted vinylepoxide linchpins proceed to deliver three-component adducts with excellent Eselectivity.

published proceedings

  • Angew Chem Int Ed Engl

altmetric score

  • 11.292

author list (cited authors)

  • Chen, M. Z., Gutierrez, O., & Smith, A. B.

citation count

  • 40

complete list of authors

  • Chen, Ming Z||Gutierrez, Osvaldo||Smith, Amos B

publication date

  • January 2014