Rhodium(I)-catalyzed allenic carbocyclization reaction affording delta- and epsilon-lactams

Org Lett. 2007 Jan 18;9(2):347-9. doi: 10.1021/ol062842u.

Abstract

This letter extends the scope of the rhodium(I)-catalyzed allenic Alder-ene carbocyclization reaction to the preparation of delta- and epsilon-lactams from amides. A variety of allenic propiolamides were cycloisomerized to give a number of unsaturated delta-lactams. In addition, allenic propargylamides give good yields of the corresponding epsilon-lactams. Formation of lactams possessing these ring sizes has rarely been accomplished via transition-metal-catalyzed carbon-carbon bond forming strategies. Thus, this approach provides an alternative strategy for synthesizing these substructures. [reaction: see text].

Publication types

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

MeSH terms

  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry*
  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Alkenes
  • Alkynes
  • Lactams
  • Rhodium