Chiral π-allylpalladium-catalyzed asymmetric allylation of imines: Replacement of allylstannanes by allylsilanes

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2614-2615

  Nakamura, Kaori ^a   Nakamura, Hiroyuki ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLYL COMPOUND; HEXANE; HYDROFLUORIC ACID; IMINE; PALLADIUM COMPLEX; TETRABUTYLAMMONIUM; TETRAHYDROFURAN DERIVATIVE; TIN DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; STEREOCHEMISTRY;

EID: 0033574380     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9901081     Document Type: Article

References (27)

1. For recent reviews of allylmetal additions, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. (b) Marshall, J. A. CHEMTRACTS 1992, 5, 75.
3. (c) Roush, W. R. In Comprehensive Organic Synthesis; Heatchcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53.
4. Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
5. For the allylation of aldehydes and imines catalyzed by bis-π-allylpalladium complexes, see: Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.
6. 4:
7. (b) Laschat, S.; Kunz, H. Synlett 1990, 51.
8. (c) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883.
9. For the palladium-catalyzed coupling reactions of organosilicone compounds, see: (a) Hatanaka, Y.; Goda, K.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6511. See also:
10. (b) Horn, K. A. Chem. Rev. 1996, 95, 1317.
11. The allylation reaction proceeded even in the presence of 0.1 equiv of TBAF in 70% yield. On the other hand, the use of 2.0 equiv of TBAF in n-hexane solvent was not effective; 4a was obtained in 45% yield.
12. 2 = tetra n-butylammonium hydrogendifluoride: Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1991, 32, 1215.
13. (a) Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 3043. For reviews, see:
14. (b) Sakurai, H. Pure Appl. Chem. 1982, 54, 1.
15. (c) Sakurai, H. Pure Appl. Chem. 1985, 57, 1759.
16. The absolute configuration of the homoallylamine 4a was determined to be R by converting it to 1-phenylbutylamine. Details are shown in ref 2.
17. The experimental procedure similar to that described in ref 3 was used again.
18. For proposed mechnisms, see: Chuit, C.; Corriu, R. J. P.; Reye C.; Young, J. C. Chem. Rev. 1993, 93, 1371.
19. (a) Hosomi, A.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987, 1517.
20. (b) Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081.
21. (c) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328, C 17
22. (d) Kira, M.; Zhang, L. C.; Kabuto C.; Sakurai, H. Organometallics 1996, 15, 5335.
23. A referee pointed out that the fluoride anion is only present in a catalytic amount; therefore turnover would require breaking the notoriously stable silicon-fluoride bond. There are few examples for the reactions using a catalytic amount of fluoride ions: see ref 9a and Noyori, R.; Yokoyama, K.; Sakata, J.; Kuwajima, I.; Nakamura, E.; Shimizu, M. J. Am. Chem. Soc. 1977, 99, 1265.
24. For preparation of allylsilanes reagents 2b and 2c, see: (a) Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8678.
25. (b) Hosomi, A.; Iguchi, H.; Sakurai, H. Chem. Lett. 1982, 223.
26. The structure and the diastereomer ratios of the resulting homoallyl alcohols were determined by comparison with the reported data: Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1981, 103, 1969.
27. Normally, in the allylation reactions of aldehydes and imines with allylmetal reagents, which would proceed via the six-membered cyclic transition state, the geometries of starting allylmetal reagents should have an effect on the corresponding products. For example, see refs 1 and 4a. See also: Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778.