Asymmetric induction reactions. VII. Palladium-catalyzed asymmetric α- allylations of carbonyl compounds using chiral sulfonamides as chiral ligands

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 5, 1997, Pages 769-777

  Hiroi, Kunio ^a   Hidaka, Akira ^a   Sezaki, Rie ^a   Imamura, Yumiko ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Asymmetric allylation; Catalytic asymmetric synthesis; Chiral ligand; Chiral sulfonamide; Palladium catalyst

Indexed keywords

ALLYL COMPOUND; CARBONYL DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CATALYST; CHIRALITY; OPTICAL ROTATION; SYNTHESIS;

EID: 0030918259     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.769     Document Type: Article

References (42)

1. Part VI: Hiroi K., Arinaga Y., Ogino T., Chem. Pharm. Bull., 42, 470-474 (1994).
2. "Catalytic Asymmetric Synthesis," ed. by Ojima I., VCH Publishers, New York, 1993; Noyori R., "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York, 1994.
3. "Catalytic Asymmetric Synthesis," ed. by Ojima I., VCH Publishers, New York, 1993; Noyori R., "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York, 1994.
4. Seyden-Penne J., "Chiral Auxiliaries and Ligands in Asymmetric Synthesis," John Wiley & Sons, New York, 1995.
5. Brunner H., Synthesis, 1988, 645-654; Blystone S. L., Chem. Rev., 89, 1663-1679 (1989); Ojima I., Clos N., Bastos C, Tetrahedron, 45, 6901-6939 (1989); Blaser H.-U., Tetrahedron: Asymmetry, 2, 843-866 (1991).
6. Brunner H., Synthesis, 1988, 645-654; Blystone S. L., Chem. Rev., 89, 1663-1679 (1989); Ojima I., Clos N., Bastos C, Tetrahedron, 45, 6901-6939 (1989); Blaser H.-U., Tetrahedron: Asymmetry, 2, 843-866 (1991).
7. Brunner H., Synthesis, 1988, 645-654; Blystone S. L., Chem. Rev., 89, 1663-1679 (1989); Ojima I., Clos N., Bastos C, Tetrahedron, 45, 6901-6939 (1989); Blaser H.-U., Tetrahedron: Asymmetry, 2, 843-866 (1991).
8. Brunner H., Synthesis, 1988, 645-654; Blystone S. L., Chem. Rev., 89, 1663-1679 (1989); Ojima I., Clos N., Bastos C, Tetrahedron, 45, 6901-6939 (1989); Blaser H.-U., Tetrahedron: Asymmetry, 2, 843-866 (1991).
9. Sawamura M., Ito Y., Chem. Rev.. 92, 857-871 (1992).
10. Brunner H., Zettlmeier W., "Handbook of Enantioselective Catalysis with Transition Metal Compounds," Vol. I, II, VCH Publishers, New York, 1993.
11. Hiroi K., Arinaga Y., Tetrahedron Lett., 35, 153-156 (1994); Hiroi K., Onuma H., Arinaga Y., Chem. Lett., 1995, 1099-1100.
12. Hiroi K., Arinaga Y., Tetrahedron Lett., 35, 153-156 (1994); Hiroi K., Onuma H., Arinaga Y., Chem. Lett., 1995, 1099-1100.
13. Hiroi K., Umemura M., Tetrahedron Lett., 33, 3343-3346 (1992); Hiroi K., Umemura M., Fujisawa A., Tetrahedron Lett., 33, 7161-7164 (1992); Hiroi K., Umemura M., Tetrahedron, 49, 1831-1840 (1993); Hiroi K., Umemura M., Fujisawa A., Chem. Pharm. Bull., 41, 666-671 (1993); Hiroi K., Umemura M., Tomikawa Y., Heterocycles. 35, 73-76 (1993).
14. Hiroi K., Umemura M., Tetrahedron Lett., 33, 3343-3346 (1992); Hiroi K., Umemura M., Fujisawa A., Tetrahedron Lett., 33, 7161-7164 (1992); Hiroi K., Umemura M., Tetrahedron, 49, 1831-1840 (1993); Hiroi K., Umemura M., Fujisawa A., Chem. Pharm. Bull., 41, 666-671 (1993); Hiroi K., Umemura M., Tomikawa Y., Heterocycles. 35, 73-76 (1993).
15. Hiroi K., Umemura M., Tetrahedron Lett., 33, 3343-3346 (1992); Hiroi K., Umemura M., Fujisawa A., Tetrahedron Lett., 33, 7161-7164 (1992); Hiroi K., Umemura M., Tetrahedron, 49, 1831-1840 (1993); Hiroi K., Umemura M., Fujisawa A., Chem. Pharm. Bull., 41, 666-671 (1993); Hiroi K., Umemura M., Tomikawa Y., Heterocycles. 35, 73-76 (1993).
16. Hiroi K., Umemura M., Tetrahedron Lett., 33, 3343-3346 (1992); Hiroi K., Umemura M., Fujisawa A., Tetrahedron Lett., 33, 7161-7164 (1992); Hiroi K., Umemura M., Tetrahedron, 49, 1831-1840 (1993); Hiroi K., Umemura M., Fujisawa A., Chem. Pharm. Bull., 41, 666-671 (1993); Hiroi K., Umemura M., Tomikawa Y., Heterocycles. 35, 73-76 (1993).
17. Hiroi K., Umemura M., Tetrahedron Lett., 33, 3343-3346 (1992); Hiroi K., Umemura M., Fujisawa A., Tetrahedron Lett., 33, 7161-7164 (1992); Hiroi K., Umemura M., Tetrahedron, 49, 1831-1840 (1993); Hiroi K., Umemura M., Fujisawa A., Chem. Pharm. Bull., 41, 666-671 (1993); Hiroi K., Umemura M., Tomikawa Y., Heterocycles. 35, 73-76 (1993).
18. Hiroi K., Yakugaku Zasshi, 115, 553-569 (1995); idem, Reviews on Heteroatom Chemistry, 14, 21-57 (1996).
19. Hiroi K., Yakugaku Zasshi, 115, 553-569 (1995); idem, Reviews on Heteroatom Chemistry, 14, 21-57 (1996).
20. Hiroi K., Kitayama R., Sato S., J. Chem. Soc., Chem. Commun., 1984, 303-304; Hiroi K., Hirasawa K., Chem. Pharm. Bull., 42, 1036-1040 (1994).
21. Hiroi K., Kitayama R., Sato S., J. Chem. Soc., Chem. Commun., 1984, 303-304; Hiroi K., Hirasawa K., Chem. Pharm. Bull., 42, 1036-1040 (1994).
22. Kinoshita I., Yokota Y., Matsumoto K., Ooi S., Kashiwabara K., Fujita J., Bull. Chem. Soc. Jpn., 56, 1067-1073 (1983); Hiroi K., Abe J., Chem. Pharm. Bull., 39, 616-621 (1991).
23. Kinoshita I., Yokota Y., Matsumoto K., Ooi S., Kashiwabara K., Fujita J., Bull. Chem. Soc. Jpn., 56, 1067-1073 (1983); Hiroi K., Abe J., Chem. Pharm. Bull., 39, 616-621 (1991).
24. Achiwa K., Chem. Lett., 1977, 777-780; idem. Heterocycles, 21, 247-250 (1979).
25. Achiwa K., Chem. Lett., 1977, 777-780; idem. Heterocycles, 21, 247-250 (1979).
26. Achiwa K., Tetrahedron Lett., 1978, 1475-1478; idem, ibid., 1978, 2583-2586.
27. Achiwa K., Tetrahedron Lett., 1978, 1475-1478; idem, ibid., 1978, 2583-2586.
28. Achiwa K., J. Am. Chem. Soc., 98, 8265-8266 (1976).
29. Baker G. L., Fritschel S. J., Stille J. R., Stille J. K., J. Org. Chem., 46, 2954-2960 (1981).
30. Okada T., Morimoto T., Achiwa K., Chem. Lett., 1990, 999-1002.
31. O'Donnell M. J., Polt R. L., J. Org. Chem., 47, 2663-2666 (1982).
32. Genet J. P., Ferround D., Juge S., Ruiz Montes J., Tetrahedron Lett., 27, 4573-4576 (1986); Genet J. P., Juge S.. Ruiz Montes J., Gaudin J.-M., J. Chem. Soc., Chem. Commun., 1988, 718-719;
33. Genet J. P., Ferround D., Juge S., Ruiz Montes J., Tetrahedron Lett., 27, 4573-4576 (1986); Genet J. P., Juge S.. Ruiz Montes J., Gaudin J.-M., J. Chem. Soc., Chem. Commun., 1988, 718-719;
34. Genet J. P., Juge S., Achi S., Mallart S., Ruiz Montes J., Levif G., Tetrahedron, 44, 5263-5274 (1988).
35. Schollkopf U., Hartwig W., Pospischil K. H., Kehne H., Synthesis, 1981, 966-971.
36. Hiroi K., Koyama T., Anzai K., Chem. Lett., 1990, 235-238.
37. Hiroi K., Abe J., Suya K., Sato S., Koyama T., J. Org. Chem., 59, 203-213 (1994).
38. Hayashi T., Kanehira K., Tsuchiya H., Kumada M., J. Chem. Soc., Chem. Commun., 1982, 1162-1164; Hayashi T., Kanehira K., Hagihara T., Kumada M., J. Org. Chem., 53, 113-120 (1988).
39. Hayashi T., Kanehira K., Tsuchiya H., Kumada M., J. Chem. Soc., Chem. Commun., 1982, 1162-1164; Hayashi T., Kanehira K., Hagihara T., Kumada M., J. Org. Chem., 53, 113-120 (1988).
40. Hiroi K., Abe J., Suya K., Sato S., Tetrahedron Lett., 30, 1543-1546 (1989).
41. Frater G., Helv. Chim. Acta, 62, 2825-2828 (1979); Tomioka K., Ando K., Takemasa Y., Koga K., J. Am. Chem. Soc., 106, 2718-2719 (1984).
42. Frater G., Helv. Chim. Acta, 62, 2825-2828 (1979); Tomioka K., Ando K., Takemasa Y., Koga K., J. Am. Chem. Soc., 106, 2718-2719 (1984).