1,2-Asymmetric Induction in the SN2′-Allylation of Organocopper and Organozinc Reagents

Journal of Organic Chemistry

Volumn 58, Issue 19, 1993, Pages 5121-5129

  Arai, Masayuki ^a   Kawasuji, Takashi ^a   Nakamura, Eiichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001692317     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00071a022     Document Type: Article

References (44)

1. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828.
2. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
3. Ann, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61.
4. Ann, N. T. Top. Curr. Chem. 1980, 88, 145.
5. Still, W. C.; McDonald, J. H., III. Tetrahedron Lett. 1980, 21, 1031.
6. Corcoran, R. C.; Ma, J. J. Am. Chem. Soc. 1992, 114, 4536.
7. Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc. 1981, 103, 1224.
8. Roush, W. R.; Michaeudes, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
9. Yamamoto, Y.; Nishii, S.; Ibuka, T. J. Chem. Soc., Chem. Commun. 1987, 464.
10. Isobe, M.; Nishikawa, T.; Herunsalee, A.; Tsukiyama, T.; Hirose, Y.; Shimokawa, K.-I.; Goto, T. Pure Appl. Chem. 1990, 62, 2007 and refs therein.
11. Matsunaga, H.; Sakamaki, T.; Nagaoka, H.; Yamada, Y. Tetrahedron Lett. 1983, 24, 3009.
12. Preliminary communication: Nakamura, E.; Sekiya, K.; Arai, M.; Aoki, S. J. Am. Chem. Soc. 1989, 111, 3091.
13. Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5515.
14. Arai, M.; Nakamura, E.; Lipshutz, B. H. J. Org. Chem. 1991, 56, 5489.
15. Arai, M. M.; Lipshutz, B. H.; Nakamura, E. Tetrahedron 1992, 48, 5709.
16. 3” reagent is also highly regioselective for the substrate D: Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 2318.
17. Arai, M.; Kawasuji, T.; Nakamura, E. Chem. Lett. 1993, 357.
18. Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. Int., Ed. Engl. 1982, 21, 135.
19. Cram, D. J.; Greene, F. D. J. Am. Chem. Soc. 1953, 75, 6005.
20. Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1985, 107, 6411.
21. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1985, 107, 2138.
22. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130.
23. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778.
24. Alexakis, A.; Marek, I.; Mageney, P.; Normant, J. F. J. Am. Chem. Soc. 1990, 112, 8042.
25. Crabbé, P.; Barreiro, E.; Dollat, J.-M.; Luche, J.-L. J. Chem. Soc., Chem. Commun. 1976, 183.
26. Dollat, J.-M.; Luche, J.-L.; Crabbé, P. J. Chem. Soc., Chem. Commun. 1977, 761.
27. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063.
28. Nakamura, E.; Kuwajima, I. Org. Synth. 1987, 66, 43.
29. Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056.
30. N2′-selective reactions of allylic bromides have been noted in some cases: Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1988, 29, 2395.
31. Heathcock, C. H.; Kiyooka, S.-I.; Blumenkopf, J. A. J. Org. Chem. 1984, 49, 4214.
32. Cf. Lehmkuhl, H. Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H., Eds.; Springer: Berlin, 1988; p 185.
33. Note that we have retracted our previous suggestion (ref 5 and Nakamura, E. Synlett 1991, 539; see ref 4 for similar suggestions for conjugate additions) based on the assumption that the nucleophilic attack of the copper atom is crucial in the allylation reaction (ref 20). This latter assumption stands in contrast to the carbometalation mechanism, in which the R group acts as a nucleophile and the copper atom as an electrophile.
34. for theoretical discussion on the electronics of carbometalation of olefins, see: Nakamura, E.; Nakamura, M.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 99.
35. Hirsch, J. A. Top. Stereochem. 1967, 1 199.
36. Karabatsos, G. J.; Fenoglio, D. J. Top. Stereochem. 1970, 5, 167.
37. Wiberg, K. B. Adv. Mol. Model. 1988, 1, 101.
38. − addition to formaldehyde. Ethylene: Houk, K. N.; Rondan, N. G.; Schleyer, P. V. R.; Kaufmann, E.; Clark, T. J. Am. Chem. Soc. 1985, 107, 2821.
39. Acetylene: Nakamura, E.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 6686.
40. Formaldehyde: Kaufmann, E.; Schleyer, P. V. R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560.
41. Bachrach, S. M.; Streitwieser A. Jr. J. Am. Chem. Soc. 1986, 108, 3946.
42. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
43. Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179.
44. Buse, C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685.