Generation and trapping of allene oxides: An approach to chiral, nonracemic α-alkoxyketones

Tetrahedron

Volumn 54, Issue 47, 1998, Pages 14265-14282

  Shipman, Michael ^a   Thorpe, Heidi R ^b   Clemens, Ian R ^c  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; OXIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; EPOXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032211325     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00878-3     Document Type: Article

References (41)

1. 1. For reviews on the chemistry of allene oxides, see (a) Chan, T.H.; Ong, B.S. Tetrahedron, 1980, 36, 2269;
2. (b) L'Abbe, G. Angew. Chem., Int. Ed. Engl., 1980, 19, 276;
3. (c) Stang, P.J. The Chemistry of Functional Groups, Supplement E: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Analogues; Patai, S., Ed.; Wiley: New York, 1983; pp 859-879;
4. (d) Smadja, W. Chem. Rev., 1983, 83, 263.
5. 2. For some leading references, see (a) Brash, A.R. J. Am. Chem. Soc., 1989, 111, 1891;
6. (b) Hamberg, M.; Fahlstadius, P. Arch. Biochem. Biophys., 1990, 276, 518;
7. (c) Song, W.-C.; Brash, A.R. Science, 1991, 253, 781;
8. (d) Brash, A.R.; Hughes, M.A.; Hawkins, D.J.; Boeglin, W.E.; Song, W.-C.; Meijer, L. J. Biol. Chem., 1991, 266, 22926;
9. (e) Lau, S.-M.C.; Harder, P.A.; O'Keefe, D.P. Biochemistry, 1993, 32, 1945;
10. (f) Brash, A.R.; Song, W.-C. J. Lipid Mediators Cell Signalling, 1995, 12, 275;
11. (g) Laudert, D.; Pfannschmidt, U.; Lottspeich, F.; Holländer-Czytko, H.; Weiler, E.M. Plant Molecular Biology, 1996, 31, 323.
12. 3. For illustrative examples, see (a) Crandall, J.K.; Machleder, W.H.; Thomas, M.J. J. Am. Chem. Soc., 1968, 90, 7346;
13. (b) Crandall, J.K.; Machleder, W.H. J. Am. Chem. Soc., 1968, 90, 7347;
14. (c) Camp, R L.; Greene, F.D. J. Am. Chem. Soc., 1968, 7349;
15. (d) Bertrand, M.; Dulcere, J. P.; Gil, G.; Grimaldi, J.; Sylvestre-Panthet, P. Tetrahedron Lett., 1976, 1507;
16. (e) Kim, S. J.; Cha, J. K. Tetrahedron Lett., 1988, 29, 5613;
17. (f) Marshall, J.A.; Tang, Y. J. Org. Chem., 1994, 59, 1457;
18. (g) Sakaguchi, S.; Watase, S.; Katayama, Y.; Sakata, Y.; Nishiyama, Y.; Ishii, Y. J. Org. Chem., 1994, 59, 5681;
19. (h) Crandall, J.K.; Rambo, E. Tetrahedron Lett., 1994, 35, 1489;
20. (i) Crandall, J.K.; Reix, T. Tetrahedron Lett., 1994, 35, 2513.
21. 4. (a) Ong, B.S.; Chan, T.H. Tetrahedron Lett., 1976, 37, 3257;
22. (b) Chan, T.H.; Ong, B.S. J. Org. Chem., 1978, 43, 2994.
23. 5. (a) Clemens, I.R.; Shipman, M.; Thorpe, H.R. Synlett, 1996, 1065;
24. (b) Clemens, I.R.; Shipman, M.; Thorpe, H.R. Tetrahedron Lett., 1997, 38, 897.
25. 6. For further examples of allene oxides generated by elimination reactions, see (a) Corey, E.J.; Ritter, K.; Yus, M.; Nájera, C. Tetrahedron Lett., 1987, 28, 3547;
26. (b) Vergne, F.; Aitken, D.J.; Husson, H.-P. J. Chem. Soc., Perkin Trans. I, 1991, 1346;
27. (c) Kabat, M.M. Tetrahedron: Asymmetry, 1993, 4, 1417;
28. (d) Kabat, M.M. Tetrahedron Lett., 1993, 34, 8543;
29. (e) Konoike, T.; Hayashi, T.; Araki, Y. Tetrahedron: Asymmetry, 1994, 5, 1559;
30. (f) Kabat, M.M. J. Org. Chem., 1995, 60, 1823;
31. (g) Kabat, M.M. Tetrahedron Lett., 1996, 37, 7437.
32. 7. Gao, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc., 1987, 109, 5765.
33. 8. (a) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem., 1986, 51, 4728;
34. (b) Katsuki, T.; Martin, V.S. Org. React., 1996, 48, 1.
35. 9. Bel-Rhlid, R.; Fauve, A.; Veschambre, H. J. Org. Chem., 1989, 54, 3221.
36. 10. Thorpe, H.R. PhD Thesis, Loughborough University, 1997.
37. 11. Sharma, S.; Oehlschlager, A.C. J. Org. Chem., 1989, 54, 5064.
38. 12. Negishi, E.; Holmes, S.J.; Tour, J.M.; Miller, J.A.; Cederbaum, F.E.; Swanson, D.R.; Takahashi, T.; J. Am. Chem. Soc., 1989, 111, 3336.
39. 13. Barton, P.; Laws, A.P., Page, M.I. J. Chem. Soc., Perkin Trans. 2, 1994, 2021.
40. 14. (a) Sonawane, H.R.; Nanjuniah, B.S.; Kulkarni, D.G.; Ahuja, J.R. Tetrahedron, 1988, 44, 7319;
41. (b) Tokunaga, Y.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 207.