Enantioselective nucleophilic substitution of a 6,6-bicyclic dienyl acetate by palladium-chiral phosphine catalyst

Chemistry Letters

Volumn , Issue 10, 1998, Pages 983-984

  Shimizu, Isao ^a   Matsumoto, Yoshiyuki ^a   Nishikawa, Masahiro ^a   Kawahara, Tamotsu ^a   Satake, Akiharu ^a   Yamamoto, Akio ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032274823     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.983     Document Type: Article

References (37)

1. a) I. Ojima, "Catalytic Asymmetric Synthesis", VHC, New York (1993).
2. b) R. Noyori, "Asymmetric Catalysis in Organic Synthesis", John Wiley & Sons, Inc., New York (1994), and other references cited therein.
3. a) C. G. Frost, J. Howarth, and J. M. J. Williams, Tetrahedron: Asymmetry, 3, 1089 (1992).
4. b) O. Reiser, Angew. Chem., Int. Ed. Engl., 32, 547 (1993).
5. c) A. Pfaltz, Acc. Chem. Res., 26, 339 (1993).
6. d) B. M. Trost and D. J. Murphy, Organometallics, 4, 1143 (1985).
7. e) T. Hayashi, A. Yamamoto, T. Hagihara, and Y. Ito, Tetrahedron Lett., 27, 191 (1986).
8. f) B. M. Trost and M. G. Organ, J. Am. Chem. Soc., 116, 10320 (1994).
9. g) G. Knühl, P. Sennhenn, and G. Helmchen, J. Chem. Soc., Chem. Commun., 1845 (1995).
10. h) T. Minami, Y. Okada, T. Otaguro, S. Tawaraya, T. Furuichi, and T. Okauchi, Tetrahedron: Asymmetry, 6, 2469 (1995).
11. i) J. Sprinz and G. Helmchen, Tetrahedron Lett., 34, 1769 (1993).
12. j) P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 32, 566 (1993).
13. (k) G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 34, 3149 (1993).
14. l) P. von Matt, G. C. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, and P. S. Pregosin, Helv. Chim. Acta, 78, 265 (1995).
15. m) T. R. Ward, Organometallics, 15, 2836 (1996).
16. n) B. M. Trost and D. L. Van Vranken, Chem. Rev., 96, 395 (1996).
17. o) B. M. Trost, T. L. Calkins, C. Oertelt, and J. Zambrano, Tetrahedron Lett., 39, 1713 (1998).
18. p) M. E. Humphries, B. P. Clark, and J. M. J. Williams, Tetrahedron: Asymmetry, 9, 749 (1998).
19. a) P. G. Andersson, and J.-E. Bäckvall, J. Org. Chem., 56, 5349 (1991).
20. b) B. M. Trost, and R. C. Bunt, Tetrahedron Lett., 34, 7513 (1993).
21. c) B. M. Trost, C. J. Urch, and M.-H. Hung, Tetrahedron Lett., 27, 4949 (1986).
22. d) B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984).
23. e) E. Curzon, B. T. Golding, C. Pierpoint, and B. W. Waters, J. Organomet. Chem., 262, 263 (1984).
24. f) B. M. Trost and R. C. Bunt, J. Am. Chem. Soc., 120, 70 (1998).
25. 2O and pyridine afforded 6 in 34% from 12.
26. J. Tsuji, I. Minami, and I. Shimizu, Tetrahedron Lett., 24, 5639 (1983).
27. 7.8 double bond by referring to the optically active authentic naphthalene derivative, which was prepared in 3 steps from the commercially available (S)-4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone.
28. a) J. Sprinz and G. Helmchen, Tetrahedron Lett., 34, 1769 (1993).
29. b) P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 32, 566 (1993).
30. c) G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 34, 3149 (1993).
31. a) B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 102, 4730 (1980)
32. b) E. Keinan and Z. Roth, J. Org. Chem., 48, 1769 (1983). In special cases, palladium-or molybdenum-catalyzed nucleophilic substitution reactions proceed with inversion via syn oxidative addition and anti nucleophile attack.
33. c) I. Stary and P. Kocovsky, J. Am. Chem. Soc., 111, 4981 (1989).
34. d) Y. D. Ward, L. A. Villanueva G. D. Allred, and L. S. Liebeskind, J. Am. Chem. Soc., 118, 897 (1996).
35. 3-allylpalladium complexes promoted by other Pd(0) complexes proceeded more rapidly in the case of monodentate phosphine ligands. K. L. Granberg and J.-E. Bäckvall, J. Am. Chem. Soc., 114, 6858 (1992).
36. B. M. Trost and R. C. Bunt, J. Am. Chem. Soc., 120, 70 (1998).
37. We confirmed that the isomerization of cis-7 to trans-7 did not take place under similar reaction conditions. Thus, by monitoring the process of the reaction with GLC, the remaining starting material, rac-6, was found to be completely racemic, and the enantiomeric excesses of the products, cis-7 and trans-7, were constant during the reaction, the fact indicating that neither kinetic resolution nor product equilibration processes are involved.