Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization

J Org Chem. 2010 May 21;75(10):3232-9. doi: 10.1021/jo100139u.

Abstract

We have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of alpha-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf)(3)) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Free Radicals / chemical synthesis
  • Free Radicals / chemistry
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Organoselenium Compounds / chemistry*
  • Stereoisomerism
  • Ultraviolet Rays

Substances

  • Free Radicals
  • Lactams
  • Mesylates
  • Organometallic Compounds
  • Organoselenium Compounds
  • ytterbium(III) triflate