A simple borohydride-based method for selective 1,4-conjugate reduction of α,β-unsaturated carbonyl compounds

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6823-6826

  Russo, Alyssa T ^a   Amezcua, Kerstin L ^a   Huynh, Vincent A ^a   Rousslang, Zach M ^a   Cordes, David B ^a  

^a PACIFIC UNIVERSITY   (United States)

Author keywords

, Unsaturated carbonyl; Conjugate reduction; Palladium catalyst; Selective reduction; Sodium borohydride

Indexed keywords

BORANE DERIVATIVE; CARBONYL DERIVATIVE;

ARTICLE; CATALYST; CONJUGATE;

EID: 80755135408     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.056     Document Type: Article

References (30)

1. S. Patai, and Z. Rappoport The Chemistry of Enones Vol. 2 1989 John Wiley & Sons Chichester
2. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 6th ed. 2007 John Wiley & Sons Hoboken, NJ
3. P.G. Andersson, and I.J. Munslow Modern Reduction Methods 2008 Wiley-VCH Verlag GmbH & Co.
4. R.C. Larock Comprehensive Organic Transformations 2nd ed. 1999 John Wiley & Sons New York
5. P.N. Rylander Hydrogenation Methods 1994 Academic Press San Diego
6. M. Hudlicky Reductions in Organic Chemistry 1984 John Wiley & Sons New York
7. P. Maki-Arvela, J. Hajek, T. Salmi, and D.Y. Murzin Appl. Catal., A 292 2005 1 49
8. K.A. De Castro, S. Oh, J. Yun, J.K. Lim, G. An, D.K. Kim, and H. Rhee Synth. Commun. 39 2009 3509 3520
9. A. Mori, T. Mizusaki, Y. Miyakawa, E. Ohashi, T. Haga, T. Maegawa, Y. Monguchi, and H. Sajiki Tetrahedron 62 2006 11925 11932
10. C.M. Belisle, Y.M. Young, and B. Singaram Tetrahedron Lett. 35 1994 5595 5598
11. W.S. Mahoney, and J.M. Stryker J. Am. Chem. Soc. 111 1989 8818 8823
12. M.D. Bhor, A.G. Panda, S.R. Jagtap, and B.M. Bhanage Catal. Lett. 124 2008 157 164
13. F.S. Tian, and S.W. Lu Synlett 2004 1953 1956
14. Y. Nishiyama, M. Yoshida, S. Ohkawa, and S. Hamanaka J. Org. Chem. 56 1991 6720 6722
15. B.C. Ranu, J. Dutta, and S.K. Guchhait Org. Lett. 3 2001 2603 2605
16. F. Alonso, I. Osante, and M. Yus Synlett 2006 3017 3020
17. P. Selvam, S.U. Sonavane, S.K. Mohapatra, and R.V. Jayaram Tetrahedron Lett. 45 2004 3071 3075
18. A. Sharma, V. Kumar, and A.K. Sinha Adv. Synth. Catal. 348 2006 354 360
19. G.R. Meyer J. Chem. Educ. 58 1981 628 630
20. D.C. Wigfield, and F.W. Gowland J. Org. Chem. 42 1977 1108 1109
21. F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry Part B: Reactions and Synthesis 1990 Plenum Press New York
22. A.L. Gemal, and J.L. Luche J. Am. Chem. Soc. 103 1981 5454 5459
23. B.C. Ranu, and S. Samanta J. Org. Chem. 68 2003 7130 7132
24. E. Keinan, and N. Greenspoon J. Am. Chem. Soc. 108 1986 7314 7325
25. R.O. Hutchins, D. Rotstein, N. Natale, J. Fanelli, and D. Dimmel J. Org. Chem. 41 1976 3328 3329
26. A. Aramini, L. Brinchi, R. Germani, and G. Savelli Eur. J. Org. Chem. 2000 1793 1797
27. A.T. Tran, V.A. Huynh, E.M. Friz, S.K. Whitney, and D.B. Cordes Tetrahedron Lett. 50 2009 1817 1819
28. G. Guella, C. Zanchetta, B. Patton, and A. Miotello J. Phys. Chem. B 110 2006 17024 17033
29. Y.Y. Titova, L.B. Belykh, L.N. Belonogova, and F.K. Shmidt Russ. J. Appl. Chem. 82 2009 1978 1985
30. 4 and then filtered through glass wool or celite. Reactions are analyzed by GC/MS.