Catalytic asymmetric allylic transfer reactions for the Enantioselective synthesis of dienyl and enynyl alcohols

European Journal of Organic Chemistry

Volumn , Issue 6, 2001, Pages 1143-1148

  Yu, Chan Mo ^a   Jeon, Miyoo ^a   Lee, Jae Young ^a   Jeon, Junha ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Alcohols; Allylation; Asymmetric catalysis; Lewis acids; Titanium

Indexed keywords

ALCOHOL; ALDEHYDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035077820     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200103)2001:6<1143::aid-ejoc1143>3.0.co;2-o     Document Type: Article

References (35)

1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, 1994, pp. 255-297.
2. K. Maruoka, H. Yamamoto, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, 1993, pp. 413-440.
3. K. Mikami, in Advances in Catalytic Process (Ed.: M. P. Doyle), JAI Press, 1995, pp. 1-44.
4. D. Hoppe, W. R. Roush, E. J. Thomas, in Stereoselective Synthesis, Vol. 3 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, 1996, pp.1357-1602.
5. M. Santell, J.-M. Pons, Lewis Acids and Selectivity in Organic Chemistry, CRC Press, 1996, pp. 91-184.
6. J. A. Marshall, Chem. Rev. 1996, 96, 31-47.
7. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
8. Y. Yanagisawa, in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer-Verlag, 1999, pp. 965-979 and references cited therein.
9. S. Casolari, P. G. Gozzi, P. Orioli, E. Tagliavini, A. UmaniRonchi, Chem. Commun. 1997, 2123-2124.
10. K. Mikami, S. Matsukawa, Nature 1997, 385, 613-615.
11. C.-M. Yu, S.-K. Yoon, S.-J Lee, J.-Y. Lee, S. S. Kim, Chem. Commun. 1998, 2749-2950.
12. C.-M. Yu, S.-J. Lee, M. Jeon, J. Chem. Soc., Perkin Trans. 1 1999, 3557-3558.
13. C.-M. Yu, S.-K. Yoon, K. Baek, J.-Y. Lee, Angew. Chem. 1998, 110, 2504-2506;
14. Angew. Chem. Int. Ed. 1998, 37, 2392-2395.
15. C.-M. Yu, H.-S. Choi, W.-H. Jung, H.-J. Kim, J. Shin, Chem. Commun. 1997, 761-762.
16. C.-M. Yu, S.-K. Yoon, H.-S. Choi, K. Baek, Chem. Commun. 1997, 763-764.
17. C.-M. Yu, H.-S. Choi, W.-H. Jung, S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
18. For example, see: K. Mori, in Total Synthesis of Natural Products, Vol. 9 (Ed.: J. Apsimon), John Wiley & Sons, 1992, pp. 280-332.
19. C. Bruneau, P. H. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. W. Rees), Pergamon, 1995, pp. 953-1085.
20. S. Weigand, R. Brückner, Liebigs Ann. 1997, 1657-1666.
21. L. A. Paquette, G. D. Bennett, M. B. Issac, A. Chhatriwalla, J. Org. Chem. 1998, 63, 1836-1845.
22. For a preparation of dilithium compound of 2-methyl-1-buten-3-yne, see: P. A. A. Klusener, W. Kulik, L. Brandsma, J. Org. Chem. 1987, 52, 5261-5266.
23. D. Weibel, V. Gevorgyan, Y. Yamamoto, J. Org. Chem. 1998, 63, 1217-1220.
24. For discussions on the additive effects in catalytic asymmetric synthesis, see: E. M. Vogl, H. Groger, M. Shibasaki, Angew. Chem. 1999, 111, 1671-1680;
25. Angew. Chem. Int. Ed. 1999, 38, 1571-1577.
26. A. L. Costra, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001-7002.
27. G. E. Keck, K. H. Tarbet, L. S. Geraci, J. Am. Chem. Soc. 1993, 115, 8467-8468.
28. G. E. Keck, D. Krishnamurthy, Org. Synth. 1997, 75, 12-18.
29. S. Weigand, R. Brückner, Chem. Eur. J. 1996, 2, 1077-1084.
30. For the asymmetric dienylboration of aldehydes using stoichiometric 2-ethenyl-2-propenylborane reagent, see: H. C. Brown, R. S. Randad, Tetrahedron 1990, 46, 4463-4472.
31. For the generation of potassium isoprene, see: L. Brandsma, H. Verkruijsse, Preparative Polar Organometallic Chemistry 2, Springer-Verlag, 1990, pp. 43-44.
32. M. Terada, K. Mikami, J. Chem. Soc., Chem. Commun. 1995, 2391-2392.
33. K. Mori, H. Takikawa, Tetrahedron 1991, 47, 2163-2168.
34. H. C. Brown, R. S. Randad, Tetrahedron Lett. 1990, 31, 455-458.
35. N. Ikeda, I. Arai, H. Yamamoto, J. Am. Chem. Soc. 1986, 108, 483-486.