Tandem reaction by using compatible catalysts: Cross-metathesis reaction and hydrogenation

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6715-6717

  Cossy, Janine ^a   Bargiggia, Frédéric C ^a   BouzBouz, Samir ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; PLATINUM DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS METATHESIS REACTION; HYDROGENATION; PURIFICATION; ROOM TEMPERATURE; TANDEM REACTION;

EID: 0037119760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01523-X     Document Type: Article

References (11)

1. Braddock D.C., Matsuno A. Tetrahedron Lett. 43:2002;3305-3308.
2. Crabtree R.H. The Organometallics Chemistry of the Transition Metals. 1988;Wiley, New York.
3. Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312-11313. and references cited therein.
4. For olefin metathesis see: (a) Fürstner, A. Alkene Metathesis in Organic Synthesis; Springer: Berlin, 1998; (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399; (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179; (e) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-221.
5. For olefin metathesis see: (a) Fürstner, A. Alkene Metathesis in Organic Synthesis; Springer: Berlin, 1998; (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399; (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179; (e) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-221.
6. For olefin metathesis see: (a) Fürstner, A. Alkene Metathesis in Organic Synthesis; Springer: Berlin, 1998; (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399; (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179; (e) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-221.
7. For olefin metathesis see: (a) Fürstner, A. Alkene Metathesis in Organic Synthesis; Springer: Berlin, 1998; (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399; (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179; (e) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-221.
8. For olefin metathesis see: (a) Fürstner, A. Alkene Metathesis in Organic Synthesis; Springer: Berlin, 1998; (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399; (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179; (e) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-221.
9. BouzBouz S., De Lemos E., Cossy J. Adv. Synth. Catal. 344:2002;0000.
10. 2 were introduced. The reaction mixture was degassed again under vacuum and then stirred under one atmosphere of hydrogen. After 15 h at rt, the solvent was evaporated and the residue was purified by flash chromatography to produce the corresponding γ-silylated carbonyl compound.
11. When the cross-metathesis products were isolated and then the hydrogenation was carried out, yields of γ-silylated carbonyl compounds were comparable to those of the one step process, but the purification of the cross-metathesis compounds was necessary.