Tandem cyclopropanation/ring-closing metathesis of dienynes.
Certain dienynes give cyclorearrangement by tandem cyclopropanation/ring-closing alkene metathesis, triggered by either a ruthenium carbene or noncarbene ruthenium(II) precatalyst. The process represents a variation of enyne metathesis where presumed cyclopropyl carbene intermediates undergo a consecutive ring-closing metathesis. A mechanistic proposal is offered, and sequential use of catalysts provided a tandem ring-closing enyne/alkene metathesis product.
Department of Chemistry, University at Buffalo, State University of New York, Buffalo, New York 14260-3000, USA.
Brian P
BP
Peppers
Steven T
ST
Diver
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; D003517:Cyclopentanes; D003521:Cyclopropanes; D012428:Ruthenium