Low catalyst loadings in olefin metathesis: synthesis of nitrogen heterocycles by ring-closing metathesis

Org Lett. 2010 Mar 5;12(5):984-7. doi: 10.1021/ol9029808.

Abstract

A series of ruthenium catalysts have been screened under ring-closing metathesis (RCM) conditions to produce five-, six-, and seven-membered carbamate-protected cyclic amines. Many of these catalysts demonstrated excellent RCM activity and yields with as low as 500 ppm catalyst loadings. RCM of the five-membered carbamate series could be run neat, the six-membered carbamate series could be run at 1.0 M, and the seven-membered carbamate series worked best at 0.2-0.05 M.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Nitrogen / chemistry*
  • Ruthenium / chemistry

Substances

  • Alkenes
  • Heterocyclic Compounds
  • Ruthenium
  • Nitrogen