On the regioselectivity of the Ru-catalyzed intramolecular [5 + 2] cycloaddition.
The influence of substituents on which cyclopropyl bond cleaves in the cycloisomerization of cyclopropylenynes catalyzed by CpRu(N&tbd1;CCH(3))(3)(+)PF(6)(-) is compared to the corresponding Rh-catalyzed reaction. With the trans cyclopropyl substrates, the bond energy of the cleaving bond appears to be an important factor. With cis cyclopropyl substrates, steric effects appear to dominate.
Trost
B M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@leland.stanford.edu
Shen
H C
HC
D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003521:Cyclopropanes / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D012428:Ruthenium
D000475:Alkenes; D000480:Alkynes; D003521:Cyclopropanes; D012428:Ruthenium