Asymmetric allylic alkylation catalyzed by palladium complexes with a new chiral bisphosphine ligand

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 375-378

  Longmire, James M ^a   Zhu, Guoxin ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; BIPHENYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031021705     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02329-5     Document Type: Article

References (32)

1. (a) Morrison, J. D. Ed. Asymmetric Synthesis, Academic Press: New York, 1985, vol.5.
2. (b) Noyori, R.; Kitamura, M. in Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin Hedelberg, 1989, vol. 5, p.115.
3. (c) Ojima, I. Ed. Catalytic Asymmetric Synthesis, VCH: New York, 1993.
4. (a) Brunner, H. in Topics in Stereochemistry; Inerterscience: New York, 1988, vol. 18, p.129.
5. (b) Brunner, H.; Zettlmeier, W. Eds. Handbook of Enantioselective Catalysis, VCH: New York, 1993, vol. 2.
6. For some examples of chiral bisphosphines in allylic alkylation, see: (a) O'Donnell, M. J.; Zhou, C.; Chen, N. Tetrahedron: Asymmetry 1996, 7, 621.
7. (b) Bricout, H.; Carpenter, J-F; Mortreux, A. Tetrahedron Lett. 1996, 37, 6105.
8. (c) Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron Lett. 1990, 31, 5049.
9. (d) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am, Chem. Soc. 1996, 118, 6297.
10. (e) Hayashi, Y.; Sakai, H.; Kaneta, N.; Uemura, M. J.Organomet.Chem. 1995, 503, 143.
11. (f) Bolm, C.; Kaufmann, D.; Gessler, S.; Harms, K. J.Organomet.Chem. 1995, 502, 47.
12. (g) Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
13. (h) Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett. 1996, 37, 4475.
14. (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
15. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
16. (a) Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649.
17. (b) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
18. (c) Trost, B. M.; Van Vranken, D. L. Angew. Chem. Int. Ed. Engl. 1992, 31, 328.
19. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
20. (e) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089.
21. Burgess, K.; Porte, A. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 1182.
22. Enantiomeric excess was measured by HPLC using a Chiracel OD column.
23. Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
24. 3) δ 2.92 (s).
25. McKinstry, L.; Livinghouse, T. Tetrahedron 1995, 51, 7655.
26. (a) Sawamura, M.; Hamashima, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549.
27. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593.
28. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem, Int. Ed. Engl. 1994, 33, 111.
29. (d) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.
30. (e) Goeke, A.; Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem. Int. Ed. Engl. 1996, 35, 662.
31. (f) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Tetrahedron Lett. 1995, 36, 5239.
32. (g) Sawmura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602.