Chiral synthesis via organoboranes. 44. Racemic and diastereo- and enantioselective homoallenylboration using dialkyl 2,3-butadien-1-ylboronate reagents. Another novel application of the tandem homologation-allylboration strategy

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 100-104

  Soundararajan, Raman ^a   Li, Guisheng ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002140598     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9513976     Document Type: Article

References (38)

1. (a) This is different from the asymmetric homologation of boronic esters which leads to α-halo boronic esters and has been studied extensively by Matteson and co-workers
2. (b) Matteson, D. S. Tetrahedron 1989, 45, 1859 and references therein.
3. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150.
4. Sadhu, K. M.; Matteson, D. S. Organometallics 1985, 4, 1687.
5. Michnik, T. J.; Matteson, D. S. Synlett 1991, 631.
6. Wallace, R. H.; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
7. Soundararajan, R ; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8957.
8. Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8961.
9. (a) For an excellent review on allylboration, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
10. (b) Brown, H. C.; Phadke, A. S.; Bhat, N. G. Tetrahedron Lett. 1993, 34, 7845.
11. (c) Brown, H. C.; Phadke, A. S. Synlett 1993, 927.
12. Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1995, 36, 2441.
13. (a) Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513.
14. (b) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1992, 953.
15. (c) Bloch, R.; C-Gradoz, N. Tetrahedron Lett. 1992, 33, 6147.
16. (d) Tebbe, M. J.; Wender, P. A. Synthesis 1991, 1059.
17. (e) Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 1893.
18. (f) Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsugi, O. Bull. Chem. Soc. Jpn. 1987, 60, 325.
19. (g) Krief, A.; Halazy, S. Tetrahedron. Lett. 1980, 21, 1997.
20. (a) Nativi, C.; Taddei, M.; Mann, A. Tetrahedron 1989, 45, 1131.
21. (b) Jenkins, P. R.; Brown, P. A. J. Chem. Soc., Perkin Trans. 1 1986, 1129.
22. (c) Jenkins, P. R.; Brown, P. A. Tetrahedron Lett. 1982, 23, 3733.
23. (d) Wada, E.; Kanemasa, S.; Fujiwara, I.; Tsuge, O. Bull. Chem. Soc. Jpn. 1985, 58, 1942.
24. (e) Nunomoto, S.; Yamashita, Y. J. Org. Chem. 1979, 44, 4788.
25. (f) Kondo, K.; Dobashi, S.; Matsumoto, M. Chem. Lett. 1976, 1077.
26. Hatakeyama, S.; Sugawara, K.; Kawanmura, M.; Takano, S. Tetrahedron Lett. 1991, 32, 4509.
27. Gridnev, I.; Kanai, G.; Miyaura, N.; Suzuki, A. J. Organomet. Chem. 1994, 481, C4.
28. All our attempts to transesterify the pinacol 2,3-butadien-1-ylboronate esters with tartrates failed.
29. 12
30. Mash, E. A. In Studies in Natural Product Chemistry; Attaur-Rahman, Ed.; Elsevier Science Publishing: New York, 1988; Vol. 1, pp 557-653.
31. 4 additions and its effects, see: Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109.
32. (b) Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 81.
33. (c) Ikeda, N.; Arai, I.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483.
34. Hope, H.; Bohm, I.; Kleinschroth, J. Org. Synth. 1981, 60, 485.
35. Liu, H.-S.; Paquette, L. A. Synth. Commun. 1994, 24, 2503
36. Brown, H. C., Jayamani, M.; Racherla, U. S. Unpublished results.
37. Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L., Viance, C. S. J. Org. Chem. 1991, 56, 4056
38. Franck-Neumann, M-.; Martina, D. M.; Heitz, M.-P. J. Organomet. Chem. 1986, 301, 61.