Substrate encapsulation: an efficient strategy for the RCM synthesis of unsaturated epsilon-lactones. Academic Article uri icon

abstract

  • A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

published proceedings

  • Org Lett

altmetric score

  • 3

author list (cited authors)

  • Pentzer, E. B., Gadzikwa, T., & Nguyen, S. T.

citation count

  • 22

complete list of authors

  • Pentzer, Emily B||Gadzikwa, Tendai||Nguyen, SonBinh T

publication date

  • November 2008