A convenient one pot allylation of aldehydes with allylic halides prepared in situ from allylic alcohols in the presence of metallic bismuth

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 3, 2000, Pages 689-692

  Miyoshi, Norikazu ^a   Nishio, Mami ^a   Murakami, Shunsuke ^a   Fukuma, Tomohiro ^a   Wada, Makoto ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; ALLYL COMPOUND; BISMUTH; HALIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034068073     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.689     Document Type: Article

References (26)

1. a) R. W. Hoffman, Angew. Chem., Int. Ed. Engl., 21, 555 (1982).
2. b) Y. Yamamoto and K. Maruyama, Heterocycles, 18, 357 (1982).
3. c) Y. Yamamoto, Acc. Chem. Res., 20, 243 (1987).
4. d) Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993), and references cited therein.
5. There have been a few reports on the allylation of aldehydes with allylic alcohols: Y. Masuyama, T. Ito, and Y. Kurusu, "72nd Annual Meeting of the Chemical Society of Japan," Tokyo, March 1997, Abstr., No. 2F202. They also reported results by using Pd-catalyst and tin(II) chloride.
6. a) Y. Masuyama, S. Mochizuki, and Y. Kurusu, Synth. Commun., 27, 1015 (1997).
7. b) Y. Masuyama, M. Kagawa, and Y. Kurusu, Chem. Commun., 1996, 1585.
8. c) J. P. Takahara, Y. Masuyama, and Y. Kurusu, J. Am. Chem. Soc., 114, 2577 (1992). Allyl sulfonates which can be readily prepared from allylic alcohols were used for the allylation in one pot: T. Imai and S. Nishida, J. Chem. Soc., Chem. Commun., 1994, 277. Recently, there have been a lot of reports on the In-mediated reaction in aqueous media, and the reactions are sometimes accelerated by protic acids. But, to our knowledge, there are no reports on the allylation of aldehydes using allylic alcohols, containing the transformation of the functional group from an allylic alcohol to an allylic halide in situ.
9. c) J. P. Takahara, Y. Masuyama, and Y. Kurusu, J. Am. Chem. Soc., 114, 2577 (1992). Allyl sulfonates which can be readily prepared from allylic alcohols were used for the allylation in one pot: T. Imai and S. Nishida, J. Chem. Soc., Chem. Commun., 1994, 277. Recently, there have been a lot of reports on the In-mediated reaction in aqueous media, and the reactions are sometimes accelerated by protic acids. But, to our knowledge, there are no reports on the allylation of aldehydes using allylic alcohols, containing the transformation of the functional group from an allylic alcohol to an allylic halide in situ.
10. a) R. Bohlmann, "Synthesis of Halides in Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 6, Chap. 1.7, pp. 203-223.
11. b) V. J. Davisson, A. B. Woodside, T. R. Neal, K. E. Stremlar, M. Muehlbacher, and C. D. Poulter, J. Org. Chem., 51, 4768 (1986).
12. c) E. J. Corey, D. E. Cane, and L. Libit, J. Am. Chem. Soc., 93, 7016 (1971).
13. d) J. A. Katzenellenbogen and A. L. Crumrine, J. Am. Chem. Soc., 98, 4925 (1976).
14. a) M. Wada, T. Fukuma, M. Morioka, T. Takahashi, and N. Miyoshi, Tetrahedron Lett., 38, 8045 (1997).
15. b) M. Wada, M. Honna, Y. Kuramoto, and N. Miyoshi, Bull. Chem. Soc. Jpn., 70, 2265 (1997).
16. c) M. Wada, H. Ohki, and K. Akiba, Bull. Chem. Soc. Jpn., 63, 1738 (1990).
17. d) M. Wada, H. Ohki, and K. Akiba, J. Chem. Soc., Chem. Commun., 1987, 708.
18. e) M. Wada, H. Ohki, and K. Akiba, Tetrahedron Lett, 27, 4771 (1986).
19. f) M. Wada and K. Akiba, Tetrahedron Lett., 26, 4211 (1985).
20. a) M. E. Jung and P. L. Ornstein, Tetrahedron Lett., 18, 2659 (1977).
21. b) G. A. Olah, A. Husain, B. P. Singh, and A. K. Mehrotra, J. Org. Chem., 48, 3667 (1983).
22. Using metallic Bi, benzaldehyde, and 1-bromo-2-butene in DMF, the corresponding homoallylic alcohol was obtained in 64% yield with the ratio of syn : anti = 77:23. See Ref. 4c.
23. a) T. Hiyama, K. Kimura, and H. Nozaki, Tetrahedron Lett., 22, 1037 (1981).
24. b) S. Matsubara, K. Wakamatsu, Y. Morizawa, N. Tsuboniwa, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 58, 1196 (1985).
25. I. Hachiya and S. Kobayashi, J. Org. Chem., 58, 6958 (1993).
26. T. Mukaiyama and T. Harada, Chem. Lett., 1981, 1527.