A convenient, efficient method for conjugate reductions using catalytic quantities of Cu(I)

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4627-4630

  Lipshutz, Bruce H ^a   Keith, John ^a   Papa, Patrick ^a   Vivian, Randall ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; COPPER DERIVATIVE; COPPER ION; REAGENT; SOLVENT; TERT BUTYL ALCOHOL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0032566023     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00855-7     Document Type: Article

References (20)

1. 1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Tarrytown, N.Y., 1992.
2. 2. Lipshutz, B.H.; Sengupta, S. Org. React. (N.Y.), 1992, 41, 135.
3. 3. For representative examples, see (a) Lipshutz, B.H.; Ung, C.; Sengupta, S. Synlett, 1989, 64;
4. (b) Semmelhack, M.F.; Stauffer, R.D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180;
5. (c) Ashby, E.C.; Lin, J.J.; Goel, A.B. ibid. 1978, 43, 183;
6. (d) Whitesides, G.M.; Filippo, J.S.; Stredronsky, E.R.; Casey, C.P. J. Am. Chem. Soc. 1969, 93, 6542;
7. (e) Boeckman, R.K.; Michalak, R. ibid. 1974, 96, 1623.
8. 4. Mahoney, W.S.; Brestensky, D.M.; Stryker, J.M. J. Am. Chem. Soc. 1988, 120, 291.
9. 2SiH, can be used catalytically. However, all examples given, as recommended in the text, involve stoichiometric amounts of Cu(I);
10. (b) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887;
11. (c) In the procedure sited above, DMI (N,N-dimethylimidazolidinone) is the recommended solvent.
12. 6. (a) Mahoney, W.S.; Stryker, J.M. J. Am. Chem. Soc. 1989, 111, 8818;
13. (b) Stryker, J.M.; Mahoney, W.S.; Daeuble, J.F.; Brestensky, D.M. In Catalysis in Organic Synthesis, Pascoe, W.E., Ed.; Marcel Dekker; New York, 1992, pp 29-44.
14. 6.
15. 8. Hays, D.S.; Fu, G.C. J. Org. Chem. 1997, 62, 7070.
16. 2siH, stable silyl enol ethers are the initial products as determined by GCMS. This could be used to advantage, e.g., as in 3-component coupling reactions; Lipshutz and Keith, ongoing work.
17. 10. This chemospecificity was anticipated based on earlier work by Stryker: Brestensky, D.M.; Stryker, J.M. Tetrahedron Lett. 1989, 30, 5677.
18. 4, vacuum filtration, and evaporation to dryness gives the crude product which is purified by Kugelrohr distillation or column chromatography on silica gel.
19. 4, filtering, and evaporation to dryness gives the crude product which is purified by Kugelrohr distillation or column chromatography on silica gel.
20. 3 combination is on the order of several days.