Chemoselective catalytic hydrogenation of alkenes by Lindlar catalyst

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 947-948

  Ghosh, Arun K ^a   Krishnan, K ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZYLAMINE; ETHER DERIVATIVE; METHANOL;

ARTICLE; CATALYSIS; CATALYST; HYDROGENATION; ORGANIC CHEMISTRY;

EID: 0032568056     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10666-9     Document Type: Article

References (10)

1. 1. For monographs on reductions, see; (a) Hudlicky, T. Reductions in Organic Chemistry, Wiley Interscience, New York, 1984;
2. (b) Augustine, L. R.; Ed. Reduction, Marcel Dekkar, New York, 1968.
3. 2. (a) Bindra, J. S.; Grodski, A. J. Org. Chem. 1978, 16, 3240;
4. (b) Caine, D.; Smith, Jr. T. L. J. Am. Chem. Soc., 1980, 102, 7570.
5. 3. (a) Czech, B. P.; Bartsch, A. R. J. Org. Chem. 1984, 49, 4076;
6. (b) Saiki, H. Tetrahedron Lett. 1995, 36, 3465.
7. 4. March, J. Advanced Organic Chemistry, Fourth edition, Wiley Interscience 1992.
8. 5. For a recent method for hydrogenation of an ene-ester in the presence of a benzyl groups and a sterically hindered N-Bn group, see, Shi, Y.; Peng, L. F.; Kishi, Y. J. Org. Chem, 1997, 62, 5666.
9. 6. In a typical procedure, a mixture of olefin (1 mmol) and Lindlar catalyst (10% by wt) in methanol (10 mL) was stirred under a hydrogen filled balloon or on a Parr apparatus under 20 psig for few hours. After this period, the mixture was filtered through a pad of celite, the solvent was evaporated and the residue was passed through a short silica gel column (50% ethyl acetate/hexane) to give the title hydrogenation product.
10. 7. Financial support of this work by the National Institute of Health (GM53386) is gratefully acknowledged.