Pauson-Khand reaction of internal dissymmetric trifluoromethyl alkynes. Influence of the alkene on the regioselectivity.
The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.
Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, Spain. nuria.aiguabella@irbbarcelona.org.
Nuria
N
Aiguabella
Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, Spain. elsa_mtz@hotmail.es.
Elsa M
EM
Arce
Department de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. Carlos.Pozo@uv.es.
Carlos
C
Del Pozo
Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, Spain. xavier.verdaguer@irbbarcelona.org.
Xavier
X
Verdaguer
Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, Spain. antoni.riera@irbbarcelona.org.
Antoni
A
Riera
D000480:Alkynes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005030:Ethylenes / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D005030:Ethylenes; D006845:Hydrocarbons, Fluorinated; D009636:Norbornanes; C013314:trifluoromethyl hypofluorite; C036216:ethylene