New route to α-adducts of homoallylic alcohols by an acid-catalyzed stereospecific allyl-transfer reaction from γ-adducts

Chemistry - A European Journal

Volumn 6, Issue 16, 2000, Pages 2909-2913

  Nokami, Junzo ^a   Anthony, Laurence ^a   Sumida, Shin Ichi ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alcohols; Allyl complexes; Allyl transfer; Allylations; Homoallylic alcohols; Reaction mechanisms

Indexed keywords

ACID; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034683091     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000818)6:16<2909::AID-CHEM2909>3.0.CO;2-2     Document Type: Article

References (53)

1. Reviews: a) G. Courtois, L. Miginiac, J. Organomet. Chem. 1974, 69, 1;
2. b) J. F. Biellmann, J. B. Ducep, Org. React. 1982, 27, 1;
3. c) W. R. Roush, Comprehensive Organic Synthesis, Vol. 2 (Ed.: C. H. Heathcock), Pergamon, Oxford, 1990, pp. 1-53;
4. d) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
5. F. Sato, K. Iida, S. Iijima, H. Moriya, M. Sato, J. Chem. Soc. Chem. Commun. 1981, 1140-1141.
6. a) Y. Okude, S. Hirano, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 3179-3181;
7. b) T. Hiyama, K. Kimura, H. Nozaki, Tetrahedron Lett. 1981, 22, 1037-1040;
8. c) T. Hiyama, Y. Okude, K. Kimura, H. Nozaki, Bull. Chem. Soc. Jpn. 1982, 55, 561-568;
9. d) C. T. Buse, C. H. Heathcock, Tetrahedron Lett. 1978, 1685-1688. For a review,
10. e) P. Cintas, Synthesis 1992, 248-257.
11. D. B. Collum, J. H. McDonald, W. C. Still, J. Am. Chem. Soc. 1980, 102, 2118-2120.
12. a) R. W. Hoffmann, H.-J. Zeiss, Angew. Chem. 1979, Angew. Chem. Int. Ed. Engl. 1979, 18, 306-307;
13. a) R. W. Hoffmann, H.-J. Zeiss, Angew. Chem. 1979, Angew. Chem. Int. Ed. Engl. 1979, 18, 306-307;
14. b) R. W. Hoffmann, H.-J. Zeiss, J. Org. Chem. 1981, 46, 1309-1314.
15. a) H. Yatagai, Y. Yamamoto, K. Maruyama, J. Am. Chem. Soc. 1980, 102, 4548-4550;
16. b) Y. Yamamoto, H. Yatagai, Y. Naruta, K. Maruyama, J. Am. Chem. Soc. 1980, 102, 7107-7109;
17. c) G. E. Keck, D. E. Abbott, E. P. Boden, E. J. Enholm, Tetrahedron Lett. 1984, 25, 3927-3930;
18. d) S. E. Denmark, E. J. Weber, T. M. Wilson, T. M.; Willson, Tetrahedron 1989, 45, 1053-1065.
19. a) A. Yanagisawa, S. Habaue, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 8955-8956;
20. b) A. Yanagisawa, S. Habaue, K. Yasue, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 6130-6141.
21. A. Gambaro, P. Ganis, D. Marton, V. Peruzzo, G. Tagliavini, J. Organomet. Chem. 1982, 231, 307-314.
22. A. Gambaro, A. Boaretto, D. Marton, G. Tagliavini, J. Organomet. Chem. 1984, 260, 255-262.
23. Y. Yamamoto, N. Maeda, K. Maruyama, J. Chem. Soc. Chem. Commun. 1983, 742-743.
24. Y. Yamamoto, K. Maruyama, J. Org. Chem. 1983, 48, 1564-1565.
25. B.-S. Guo, W. Doubleday, T. Cohen, J. Am. Chem. Soc. 1987, 109, 4710-4711.
26. J. Iqubal, S. P. Joseph, Tetrahedron Lett. 1989, 30, 2421-2422.
27. See ref. [6b) ].
28. A. H. McNeill, E. J. Thomas, Tetrahedron Lett. 1990, 31, 6239-6242.
29. H. Miyake, K. Yamamura, Chem. Lett. 1992, 1369-1372.
30. 2O-Sn: K. Kanagawa, Y. Nishiyama, Y. Ishii, J. Org. Chem. 1992, 57, 6988-6991; and
31. 2/ultra-sonication: Y. Masuyama, A. Hayakawa, Y. Kurusu, J. Chem. Soc. Chem. Commun. 1992, 1102-1103;
32. Ref. [6c) ].
33. J. Nokami, K. Yoshizane, H. Matsuura, S. Sumida, J. Am. Chem. Soc. 1998, 120, 6609-6610.
34. 4-induced π-cyclization reaction of methyl 2-acetoxy-2-(3-alken-1-oxy)acetate to five- and six-membered-ring ethers proceeds by a 2-oxonia [3.3]-sigmatropic rearrangement:
35. b) L. D. M. Lolkema, C. Semeyn, L. Ashek, H. Hiemstra, W. N. Speckamp, Tetrahedron, 1994, 50, 7129-7140. Many other intramolecular C-C bond formation reactions that proceed by an intramolecular Prins reaction of an oxycarbenium ion with π-nucleophile have been investigated for the syntheses of five- and six-membered cyclic ethers:
36. c) M. H. Hopkins, L. E. Overman, G. M. Rishton, J. Am. Chem. Soc., 1991, 113, 5354-5365.
37. d) W. H. Bunnelle, D. W. Seamon, D. L. Mohler, T. F. Ball, D. W. Thompson, Tetrahedron Lett. 1984, 25, 2653-2654;
38. e) A. Boaretto, D. Furlani, D. Marton, G. Tagliavini, A. Gambaro, J. Organomet. Chem., 1986, 299, 157-167;
39. f) L. Coppi, A. Ricci, M. Taddei, Tetrahedron Lett. 1987, 28, 973-976;
40. g) Z. Y. Wei, J. S. Li, D. Wang, T. H. Chan, Tetrahedron Lett., 1987, 28, 3441-3444;
41. h) A. Mekhalfia, I. E. Markó, H. Adams, Tetrahedron Lett. 1991, 32, 4783-4786;
42. i) I. E. Markó, F. Chellé, Tetrahedron Lett. 1997, 38, 2895-2898;
43. j) D. Hoppe, T. Krämer, C. F. Erdbrügger, E. Egert, Tetrahedron Lett. 1989, 30, 1233-1236;
44. k) J. S. Panek, R. Beresis, J. Org. Chem., 1993, 58, 809-811;
45. l) R. W. Hoffman, V. Giesen, M. Fuest, Liebigs, Ann. Chem., 1993, 629-639;
46. 4) to give chlorinated cyclic ethers, etc.
47. The reaction conditions shown in Table 1 (entry 5) were applicable.
48. Treatment using higher concentrations (0.5 M) and/or longer reaction times (4-5 h) resulted in an increase of (E)-14d with lower optical purity, and the incomplete consumption of the starting material, syn13d.
49. a) W. R. Roush, K. Ando, D. B. Powers, R. L. Halterman, A. D. Palkowitz, Tetrhaedron Lett. 1988, 29, 5579-5582;
50. b) W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz, R. L. Halterman, J. Am. Chem. Soc. 1990, 112, 6339-6348.
51. Hydrogen chloride (1.0M solution in anhydrous ether; purchased from Aldrich) was effective for this reaction.
52. It seems reasonable that the additives would serve as a Lewis acid for the common allylation by an inactive allylic metal such as 4 to give the syn-γ-adduct 2 predominantly, and then as a catalyst for the allyl-transfer reaction from γ to α with Z selectively. However, the actual catalyst for the reaction is not completely clear, because a Brønsted acid such as HCl also served as a good catalyst, and will be easily formed from a Lewis acid with alcohol (substrate of the reaction) or moisture.
53. 2 to give good results, many of the previously reported α-allylation reactions (described in A) were performed at a lower temperature for shorter reaction times with more than stoichiometric amounts of additives. It should be noted, however, that the in situ formed γ-adduct (Lewis acid complex) derived from an aldehyde and an allylic metal with additive (Lewis acid), would be much more reactive than the corresponding alcohol used in our reaction. The complex would smoothly react with a large amount of unreacted aldehyde, existing in the reaction mixture before the reaction with allylic metal, to give the oxycarbenium ion. We believe that this allyl-transfer reaction will play an important role in many α-selective allylation reactions.