Diastereoselective heterogeneous catalytic hydrogenation of Baylis- Hillman adducts

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2533-2536

  Mateus, Cristiano R ^a   Almeida, Wanda P ^b   Coelho, Fernando ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b PAULISTA UNIVERSITY   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; HYDROGENATION; STEREOCHEMISTRY;

EID: 0034620933     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00258-6     Document Type: Article

References (17)

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10. Standard experimental protocol: To a suspension of Pd-C 5% (5 mol%) in ethyl acetate (3mL) was added under nitrogen atmosphere a solution of the adduct (0.1-0.3 mmol) in 3 mL of ethyl acetate. Then the atmosphere reaction was changed for hydrogen and the reaction was maintained for 2-3 h under stirring at room temperature (for the acetylated adducts the reaction was stopped after 30 min). After that the reaction was filtrated over a pad of Celite and the solvent was removed under reduced pressure.
11. In the hydrogenation reaction of the double bond of the nitro derivatives we have observed they were totally reduced to the amine. However the diastereoselectivity achieved is comparable with the other examples.
12. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1984; Vol. 3, part B, p. 115.
13. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
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15. 2O), 3.72 (s, 3H), 4.65 (d, J=8.7 Hz, 1H), 5.94 (s, 2H), 6.84 (s, 3H).
16. (a) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860;
17. (b) Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663 and references cited therein.