A synthesis of trisubstituted alkenes by a Ru-catalyzed addition.
Catalyzed by ruthenium trisacetonitrile hexafluorophosphate 4, the Alder-ene type reaction of alkenes and internal alkynes provides an effective way to synthesize trisubstituted alkenes. Unlike most typical olefination protocols, this reaction is atom economical, and affords trisubstituted alkenes with defined olefin geometry. The regioselectivity can be explained invoking a steric argument based on the proposed mechanism. The first C-C bond formation generally involves sterically less hindered carbons of the alkenes and alkynes. Modest to very high regioselectivity can be achieved depending on the steric difference of the two substituents of alkynes.
Trost
Barry M
BM
Department of Chemistry, Stanford University Stanford, CA 94305-5080, USA. bmtrost@Ieland.stanford.edu
Shen
Hong C
HC
Pinkerton
Anthony B
AB
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*
D000475:Alkenes; D000480:Alkynes; D012428:Ruthenium