Raney nickel: An efficient reagent to achieve the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds

Synlett

Volumn , Issue 10, 1999, Pages 1663-1666

  Barrero, Alejandro F ^a   Alvarez Manzaneda, E J ^a   Chahboun, Rachid ^a   Meneses, R ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

1,4 addition; Hydrogenation

Indexed keywords

CARBONYL DERIVATIVE; NICKEL; REAGENT;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; HYDROGENATION; REDUCTION;

EID: 0032872366     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2908     Document Type: Article

References (17)

1. Ojima, I.; Kogure, T.; Nagai, Y. Tetrahedron Letters 1972, 5035-5038.
2. Fortunato, J.M.; Ganem, B. J. Org Chem. 1976, 41, 2194-2200.
3. Leutenegger, U.; Madin, A.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1989, 28, 60.
4. Semmelhack, M.F.; Stauffer, R.D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180-3188.
5. Masamune, S.; Bates, G.S.; Georghin, P.E. J. Am. Chem. Soc. 1974, 96, 3686-3688.
6. Ashby, E.C.; Lin, J-J, Goel, A.B. J. Org. Chem. 1978, 43, 183-188.
7. Osborn, M.E.; Pegues, J.F.; Paquette, L.A. J. Org. Chem. 1980, 45, 167-168.
8. Mahoney, W.S.; Brestenky, D.M.; Stryker, J.M. J. Am. Chem. Soc. 1988, 110, 291-293.
9. Keinam, E.; Greenspoon, N. J. Am. Chem. Soc. 1986, 108, 7314-7325.
10. Tanke, R.S.; Crabtree, R,H, Tetrahedron Lett. 1988, 29, 6737-6740.
11. Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96-98.
12. Freifelder, M. Catalytic Hydrogenation in Organic Synthesis: Procedures and Commentary; Wiley-Interscience: New York, 1978.
13. Rylander, P.N. Catalytic Hydrogenation in Organic Syntheses. Academic Press: New York, 1979.
14. 3), 4.33 (t, J=5.3 Hz, 1H, H-6'), 4.43 (s, 1H, H-1 ″A), 4.85 (s, 1H, H-1 ″B).
15. Barrero, A. F.; Manzaneda, E.A.; Altarejos, J.; Salido, S.; Ramos, J.M.; Simmonds, M.S.J.; Blaney, W.M. Tetrahedron 1995, 51, 7435-7450.
16. Barrero, A.F.; Cortés, M.; Manzaneda, E.A.; Cabrcra, E.; Chahboun, R.; Lara, M.; Rivas, A.R. J. Nat. Prod. 1999 (in press).
17. Typical experimental procedure: 0.8 g of an aqueous suspension of RanEy Nickel (Fluka, cat. no. 83440) was added to a stirred solution of compound (1.0 mmol) in tetrahydrofuran (10 ml) and the mixture was further stirred at room temperature (except for compound 1a, which was reacted at 0°C) for the specified time (Table). The mixture was diluted with ether and filtered through silica gel, and the solvent was evaporated to yield the reduced compound.