Catalytic Asymmetric Carbalkoxyallylation of Imines with the Chiral Bis-π-allylpalladium Complex

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3562-3564

  Fernandes, Rodney A ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLICS; CARBOXYLATION; COMPLEXATION; NITROGEN COMPOUNDS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

AYMMETRIC SYNTHESIS; CARBALKOXYALLYLATION; CHIRL 2-(2-ARYL-2-AMINO-ETHYL)ACRYLATES; PROCHIRAL IMINES;

CATALYSIS;

ACRYLIC ACID DERIVATIVE; ALLYL COMPOUND; IMINE; METAL COMPLEX; PALLADIUM COMPLEX; TIN DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 2442439837     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049838l     Document Type: Article

References (36)

1. For recent reviews on allylmetal additions, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595.
2. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, Germany, 2000; Chapter 10.
3. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, Germany, 2000; Chapter 11.
4. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
5. (e) Bloch, R. Chem. Rev. 1998, 98, 1407.
6. (f) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
7. (g) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
8. For leading references on asymmetric allylation of imines, see: (a) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896.
9. (b) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1999, 64, 4844.
10. (c) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
11. For leading references on fluoride- or alkoxide-promoted allylation of imines with allylsilanes see: (a) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
12. (b) Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 1999, 64, 4233.
13. (c) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
14. (d) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901.
15. (e) Sakurai, H. Synlett 1989, 1.
16. For allylation of N-acylhydrazones see: (a) Berger, R.; Rabbat, P. M. A. ; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 9596.
17. (b) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610.
18. (c) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493.
19. (d) Friestad, G. K.; Ding, H. Angew. Chem., Int. Ed. 2001, 40, 4491.
20. (e) Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942.
21. (f) Manabe, K.; Oyamada, H.; Sugita, K.; Kobayashi, S. J. Org. Chem. 1999, 64, 8054.
22. (a) Nyzam, V.; Belaud, C.; Zammattio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 7, 1835.
23. (b) Dembele, Y. A.; Belaud, C.; Villieras, J. Tetrahedron: Asymmetry 1992, 3, 511.
24. (c) Dembele, Y. A.; Belaud, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 3, 351.
25. Chataigner, I.; Zammattio, F.; Lebreton, J.; Villieras, J. Synlett 1998, 275.
26. (a) Felpin, F.-X.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305.
27. (b) Wright, D. L.; Schulte, J. P., II; Page, M. A. Org. Lett. 2000, 2, 1847.
28. (a) Fernandes, R. A.; Yamamoto, Y. J. Org. Chem. 2004, 69, 735.
29. (b) Fernandes, R. A.; Stimac, A.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 14133.
30. (c) Bao, M.; Nakamura, H.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 131.
31. (d) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. For the use of allyltrimethylsilane instead of allyltributylstannane, see ref 3c.
32. Nakamura, H.; Iwama, H.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1273.
33. (a) Legros, J.; Meyer, F.; Coliboeuf, M.; Crousse, B.; Bonnet-Delpon, D. ; Begue, J.-P. J. Org. Chem. 2003, 68, 6444.
34. (b) Choudhury, P. K.; Foubelo, F.; Yus, M. J. Org. Chem. 1999, 64, 3376 and references therein.
35. The carbethoxyallylstannane 2c was prepared following a literature report, see: Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
36. Singh, S. B. Tetrahedron Lett. 1995, 36, 2009.