Asymmetric Induction of the Iodolactonization Reaction of α-Sulfurated γ-Unsaturated Amides

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1196-1201

  Blot, Virginie ^a   Reboul, Vincent ^a   Metzner, Patrick ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN; STEREOCHEMISTRY; SULFUR;

ASYMMETRIC INDUCTION; IODOLACTONIZATION REACTIONS;

AROMATIC HYDROCARBONS;

AMIDE; IODINE; OXYGEN; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; IODINATION; LACTONIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 1242285047     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035488b     Document Type: Article

References (39)

1. Robin, S.; Rousseau, G. Tetrahedron 1998, 54, 13681-13736.
2. For a recent example: Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695-1702.
3. For a recent example: Macritchie, J. A.; Peakman, T. M.; Silcock, A.; Willis, C. L. Tetrahedron Lett. 1998, 39, 7415-7418.
4. For a recent example: Rozner, E.; Liu, Y. Org. Lett. 2003, 5, 181-184.
5. Ha, H.-J.; Lee, S.-Y.; Park, Y.-S. Synth. Commun. 2000, 30, 3645-3650.
6. (a) Ogu, K.-I.; Akazome, M.; Ogura, K. Tetrahedron Lett. 1998, 39, 305-308.
7. (b) Nubbemeyer, U. J. Org. Chem. 1996, 61, 3677-3686.
8. (a) Anderson, J. C.; Flaherty, A. J. Chem. Soc., Perkin Trans. 1 2001, 267-269.
9. (b) Mues, H.; Kazmaier, U. Synlett 2000, 7, 1004-1006.
10. (a) Lee, C. W.; Gil, J. M.; Oh, D. Y. Heterocycles 1997, 45, 943-948.
11. (b) Zhao, Y.; Pei, C.; Wong, Z.; Xi, S. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 66, 115-125.
12. An example with a phenylsulfonyl group has been described, but the stereochemistry of the lactone was not mentioned: Lee, J. W.; Oh, D. Y. Heterocycles 1990, 31, 1417-1421. Lee, J. W.; Jung, J. H.; Oh, D. Y. Bull. Korean Chem. Soc. 1994, 15, 842-845.
13. An example with a phenylsulfonyl group has been described, but the stereochemistry of the lactone was not mentioned: Lee, J. W.; Oh, D. Y. Heterocycles 1990, 31, 1417-1421. Lee, J. W.; Jung, J. H.; Oh, D. Y. Bull. Korean Chem. Soc. 1994, 15, 842-845.
14. Moon, H.-S.; Eisenberg, S. W. E.; Wilson, M. E.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1994, 59, 6504-6505.
15. Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297-300.
16. Nowaczyk, S.; Alayrac, C.; Reboul, V.; Metzner, P.; Averbuch-Pouchot, M.-T. J. Org. Chem. 2001, 66, 7841-7848.
17. It is also possible to carry out this reaction without isolation of 2.
18. 3: 80% yield and 90:10 dr.
19. Mukaiyama, T.; Uchiro, H.; Shiina, I.; Kobayashi, S. Chem. Lett. 1990, 1019-1022.
20. Dr was measured before purification, as epimerization on the asymmetric center in position 3 easily takes place on silica gel.
21. (a) Maligres, P. E.; Weissman, S. A.; Upadhyay, V.; Cianciosi, S. J.; Reamar, R. A.; Purick, R. M.; Sager, J.; Rossen, K.; Eng, K. K.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron 1996, 52, 3327-3338.
22. (b) LeBlond, C. R.; Rossen, K.; Gortsema, F. P.; Zavialov, I. A.; Cianciosi, S. J.; Andrews, A. T.; Sun, Y. Tetrahedron Lett. 2001, 42, 8603-8606.
23. In these conditions, some variation of dr between the lactone and the iodohydrin was observed (Table 1; entries 4, 5, 7, and 8) without any rational explanation.
24. Kantlehner, W.; Gutbrod, H.-D. Liebigs Ann. Chem. 1980, 1677-1688.
25. Handa, Y.; Inanaga, J.; Yamaguchi-ku, M. J. Chem. Soc. Chem. Commun. 1989, 298-299.
26. Prepared from (R)-dihydro-5-(hydroxymethyl)-2(3H)-furanone by iodation: Artis, D. R.; Cho, I.-S.; Jaime-Figueroa, S.; Muchowski, J. M. J. Org. Chem. 1994, 59, 2456-2466.
27. Tamaru, Y.; Mizutani, M.; Furukawa, Y.; Kawamura, S.; Yoshida, Z.; Yanagi, K.; Minobe, M. J. Am. Chem. Soc. 1984, 106, 1079-1085.
28. In this case, the imidate salt was not hydrolyzed by water. See ref 8b.
29. This model was suggested by one of the three reviewers.
30. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307-5308. See also ref 7a.
31. Chamberlin, A. R.; Dezube, M.; Dussault, P., McMills, M. C. J. Am. Chem. Soc. 1983, 105, 5819-5825. Chamberlin, A. R.; Mulholland, R. L.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672-677.
32. Chamberlin, A. R.; Dezube, M.; Dussault, P., McMills, M. C. J. Am. Chem. Soc. 1983, 105, 5819-5825. Chamberlin, A. R.; Mulholland, R. L.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672-677.
33. Kagan, H. B.; Ronan, B. Rev. Heteroatom Chem. 1992, 7, 92-116.
34. 2.
35. Still, I. W. J.; Hasan, S. K.; Turnbull, K. Synthesis 1977, 468-469.
36. 10) of 6b.
37. Kitagawa, O.; Hanano, T.; Hirata, T.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1992, 33, 1299-1302.
38. Raghavan, S.; Rasheed, A.; Joseph, S. C.; Rajender, A. Chem. Commun. 1999, 1845-1846.
39. Martin, V. S.; Rodriguez, C. M.; Martin, T. Org. Prep. Proced. Int. 1998, 30, 291-324.