Chiral epoxides as a source of chiral β-oxidofunctionalised organolithium compounds: Reaction with electrophiles

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2997-3008

  Bachki, Abderrazak ^a   Foubelo, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; ALKANOL; CYCLOALKANOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030272170     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00390-4     Document Type: Article

References (40)

1. 1. For general information, see: Asymmetric Synthesis, Vols. 1-5, Morrison, J. D. Ed.; Academic Press, Inc.: New York, 1983-1985.
2. 2. Seebach, D.; Hungerbüler, E. In Modem Synthetic Methods 1980, Scheffold, R. Ed.; Salle+Sanerländer-Verlag: Aarau, 1980.
3. 3. See, for instance: Haines, A. H. In Comprehensive Organic Chemistry Barton, D.; Olleis, W. D.; Stoddart, J. F. Eds.; Pergamon Press: Oxford, 1979; Vol. 1, pp. 866-870.
4. 4. Bartmann, E. Angew. Chem. Int. Ed. Engl. 1986, 25, 653-654.
5. 5. For the first report on this reaction, see: Barluenga, J.; Flórez, J.; Yus, M. J. Chem. Soc., Chem. Commun. 1982, 1153-1154.
6. 6. For the first report on this reaction, see: Barluenga, J.; Fañanâs, F. J.; Yus, M.; Asensio, G. Tetrahedron Lett. 1978, 2015-2016.
7. 7. Hydroxymercurials are easily available by hydroxymercuration of olefins; see, for instance: Larock, R. C. Organomercuric Compounds in Organic Synthesis; Springer Verlag: Heidelberg, 1985.
8. 8. For a review, see: Nájera, C.; Yus, M. Trends Org. Chem, 1991, 2, 155-181.
9. 9. For a comparative study of these both arenes, see: Holy, N. L. Chem. Rev. 1974, 74, 243-277.
10. 10. (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
11. (b) Yus, M. Chem. Soc. Rev., in the press.
12. 11. For the last paper on this field from our laboratory, see: Huerta, F. F.; Gómez, C.; Yus, M. Tetrahedron 1996, 52, 8333-8340.
13. 12. For the last paper on this field from our laboratory, see: Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1996, 52, 8545-8564.
14. 13. For the last paper on this fild from our laboratory, see: Guijarro, A.; Yus, M. Tetrahedron 1996, 52, 1797-1810.
15. 14. For the last paper on this field from our laboratory, see: Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 11457-11464.
16. 2 reagents following Seebach's nomenclature: Seebach, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258.
17. 16. Nájera, C.; Yus, M.; Seebach, D. Helv. Chim. Acta 1984, 67, 289-300.
18. 17. Conrow, R. E. Tetrahedron Lett. 1993, 34, 5553-5554.
19. 18. Preliminary communication: Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron: Asymmetry 1995, 6, 1907-1910.
20. 19b so they have to be manipulated at temperatures below -78°C. (a) This decompositon has been used for the regio non-stereoselective preparation of olefins; for the first paper on this topic, see: Barluenga, J.; Yus, M.; Bernad, P. J. Chem. Soc., Chem. Commun. 1978, 847.
21. (b) See, for instance: Bates, R. B.; Kroposki, L. M.; Potter, D. E. J. Org. Chem. 1972, 37, 560-562.
22. 20. The enantiomeric purity of the obtained products is related to the starting materials 1, since no racemisation has ever occurred for this type of systems; see, for instance, references 16 and 17.
23. nLi at -78°C and chloromethyl methyl ether at -78 to 20°C in 96% yield.
24. 22. For a recent paper on polyols chains, see: Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron Lett. 1995, 51, 5299-5314.
25. 23. Moriarty, R. M.; Enache, L. A.; Kinney, W. A.; Alien, C. S.; Canary, J. W.; Tuladhar, S. M.; Guo, L. Tetrahedron Lett. 1995, 36, 5139-5142.
26. 24. Seving, A.; Cense, J. M. Bull. Soc. Chim. Fr. 1974, 963-968.
27. 25. Barluenga, J.; Fernández-Simón, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Chem. Commun. 1986, 1665.
28. D value not only for epoxide 11 but also for products 13e-g.
29. 27. Almena, J.; Foubelo, F.; Yus, M. J. Org. Chem. 1994, 59, 3210-3215.
30. 28. Gokel, G. W.; Dishong, D. M.; Diamond, C. J. J. Chem. Soc., Chem. Commun. 1980, 1053-1055.
31. 29. Cazaux, L.; Maroni, P. Bull Soc. Chim. Fr., 1972, 773-779. Chem. Abstr. 1972, 76, 153136t.
32. 29. Cazaux, L.; Maroni, P. Bull Soc. Chim. Fr., 1972, 773-779. Chem. Abstr. 1972, 76, 153136t.
33. 30. Bracher, F.; Litz, T. J. Prakt. Chem. 1994, 336, 608-610. Chem. Abstr. 1995, 122, 31034f.
34. 30. Bracher, F.; Litz, T. J. Prakt. Chem. 1994, 336, 608-610. Chem. Abstr. 1995, 122, 31034f.
35. 3 requires: C, 59.23; H, 11.18).
36. 32. Esafov, V. L. Org. Khim. 1971, 172-206. Chem. Abstr. 1972, 77, 151392v.
37. 32. Esafov, V. L. Org. Khim. 1971, 172-206. Chem. Abstr. 1972, 77, 151392v.
38. 33. Powers, T. S.; Shi, Y.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884.
39. 34. Corey, E. J.; Gras, J. L.; Ulrich, P. Tetrahedron Lett. 1976, 809-812.
40. 35. Ticozzi, C.; Zanarotti, A. Tetrahedron Lett. 1994, 35, 7421-7424.