10,10′ -biisopinocampheol - A new pinane derivative with C2 symmetry

Polish Journal of Chemistry

Volumn 72, Issue 11, 1998, Pages 2371-2377

  Markowicz, S W ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Bipinene; C2 symmetry; Chiral auxiliary; Myrtenyl bromide; Pinene

Indexed keywords

EID: 0032345790     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Brown H.C. and Zweifel G., J. Am. Chem. Soc., 83, 254, (1961); for reviews see: Brown H.C. and Singaram B.C., Acc. Chem. Res., 21, 287, (1988); Matteson D.S., Acc. Chem. Res., 21, 294, (1988); Matteson D.S., Chem. Rev., 1535 (1989); Matteson D.S., Stereodirected Synthesis with Organoboranes, Springer, Berlin, pp. 162-220 (1995).
2. Brown H.C. and Zweifel G., J. Am. Chem. Soc., 83, 254, (1961); for reviews see: Brown H.C. and Singaram B.C., Acc. Chem. Res., 21, 287, (1988); Matteson D.S., Acc. Chem. Res., 21, 294, (1988); Matteson D.S., Chem. Rev., 1535 (1989); Matteson D.S., Stereodirected Synthesis with Organoboranes, Springer, Berlin, pp. 162-220 (1995).
3. Brown H.C. and Zweifel G., J. Am. Chem. Soc., 83, 254, (1961); for reviews see: Brown H.C. and Singaram B.C., Acc. Chem. Res., 21, 287, (1988); Matteson D.S., Acc. Chem. Res., 21, 294, (1988); Matteson D.S., Chem. Rev., 1535 (1989); Matteson D.S., Stereodirected Synthesis with Organoboranes, Springer, Berlin, pp. 162-220 (1995).
4. Brown H.C. and Zweifel G., J. Am. Chem. Soc., 83, 254, (1961); for reviews see: Brown H.C. and Singaram B.C., Acc. Chem. Res., 21, 287, (1988); Matteson D.S., Acc. Chem. Res., 21, 294, (1988); Matteson D.S., Chem. Rev., 1535 (1989); Matteson D.S., Stereodirected Synthesis with Organoboranes, Springer, Berlin, pp. 162-220 (1995).
5. Brown H.C. and Zweifel G., J. Am. Chem. Soc., 83, 254, (1961); for reviews see: Brown H.C. and Singaram B.C., Acc. Chem. Res., 21, 287, (1988); Matteson D.S., Acc. Chem. Res., 21, 294, (1988); Matteson D.S., Chem. Rev., 1535 (1989); Matteson D.S., Stereodirected Synthesis with Organoboranes, Springer, Berlin, pp. 162-220 (1995).
6. Markowicz S.W., Karolak-Wojciechowska J. and Kwiatkowski W., J. Cryst. Spec. Res., 19, 535 (1989) and references cited therein.
7. Girard Ch. and Kagan H.B., Tetrahedron: Asymmetry, 8, 3851 (1997); for reviews see; Avalos M., Babiano R., Cintas P., Imenez J.L. and Palacios J.C., Tetrahedron: Asymmetry, 8, 2997 (1997).
8. Girard Ch. and Kagan H.B., Tetrahedron: Asymmetry, 8, 3851 (1997); for reviews see; Avalos M., Babiano R., Cintas P., Imenez J.L. and Palacios J.C., Tetrahedron: Asymmetry, 8, 2997 (1997).
9. Brown H.C. and Joshi N.N., J. Org. Chem., 53, 4059 (1988); Brown H.C., Weissman S.A., Perumal P.T. and Dhokte U.P., J. Org. Chem., 55, 1217 (1990); Brown, H.C. and Dhokte U.P., J. Org. Chem., 59, 2365 (1994).
10. Brown H.C. and Joshi N.N., J. Org. Chem., 53, 4059 (1988); Brown H.C., Weissman S.A., Perumal P.T. and Dhokte U.P., J. Org. Chem., 55, 1217 (1990); Brown, H.C. and Dhokte U.P., J. Org. Chem., 59, 2365 (1994).
11. Brown H.C. and Joshi N.N., J. Org. Chem., 53, 4059 (1988); Brown H.C., Weissman S.A., Perumal P.T. and Dhokte U.P., J. Org. Chem., 55, 1217 (1990); Brown, H.C. and Dhokte U.P., J. Org. Chem., 59, 2365 (1994).
12. See Ref. [1] and: Tomioka K., Synthesis, 541 (1990); Noyori R. and Kitamura M., Angew. Chem. Int. Ed. Eng., 1, 49 (1991); Brunner H. and Zettelmeier W., Handbook of Enantioselective Catalysis with Transition Metal Compounds, vol. I, II, VCH Publishers, Weinheim, Germany, 1993.
13. See Ref. [1] and: Tomioka K., Synthesis, 541 (1990); Noyori R. and Kitamura M., Angew. Chem. Int. Ed. Eng., 1, 49 (1991); Brunner H. and Zettelmeier W., Handbook of Enantioselective Catalysis with Transition Metal Compounds, vol. I, II, VCH Publishers, Weinheim, Germany, 1993.
14. See Ref. [1] and: Tomioka K., Synthesis, 541 (1990); Noyori R. and Kitamura M., Angew. Chem. Int. Ed. Eng., 1, 49 (1991); Brunner H. and Zettelmeier W., Handbook of Enantioselective Catalysis with Transition Metal Compounds, vol. I, II, VCH Publishers, Weinheim, Germany, 1993.
15. See Ref. 5 and, for example: Yamamoto H., Kobayashi S. and Kanemasa S., Tetrahedron: Asymmetry, 7, 149 (1996).
16. Rupe H. and Heritier A., Lieb. Ann. Chem., 459, 179 (1927).
17. Oppolzer W., Tetrahedron Letters, 23, 3901 (1982) and references cited therein.
18. Badjah-Hadj-Ahmed A.Y. and Meklati B.Y., Magn. Res. Chem., 30, 807 (1992).
19. Coxon J.M., Hydes G.J. and Steel P.J., J. Chem. Soc. Perkin Trans. II, 1351 (1984).
20. Uzarewicz I. and Uzarewicz A., Rovz. Chem., 50, 1315 (1976); Shundo R., Matsubara Y., Hishiguchi I. and Hirashima T., Bull. Chem. Soc. Jpn., 65, 530 (1992).
21. Uzarewicz I. and Uzarewicz A., Rovz. Chem., 50, 1315 (1976); Shundo R., Matsubara Y., Hishiguchi I. and Hirashima T., Bull. Chem. Soc. Jpn., 65, 530 (1992).
22. Ohloff G., Farnow H. and Shade G., Chem. Ber., 89, 1549 (1959); Harwood L.M. and Julia M., Synthesis, 6, 456 (1980); Umberit M.A. and Sharpless, K.B., J. Am. Chem. Soc., 99, 5526 (1977); de Richter R.K., Bonato M., Follet M. and Kamenka, J-M., J. Org. Chem., 55, 2855 (1990).
23. Ohloff G., Farnow H. and Shade G., Chem. Ber., 89, 1549 (1959); Harwood L.M. and Julia M., Synthesis, 6, 456 (1980); Umberit M.A. and Sharpless, K.B., J. Am. Chem. Soc., 99, 5526 (1977); de Richter R.K., Bonato M., Follet M. and Kamenka, J-M., J. Org. Chem., 55, 2855 (1990).
24. Ohloff G., Farnow H. and Shade G., Chem. Ber., 89, 1549 (1959); Harwood L.M. and Julia M., Synthesis, 6, 456 (1980); Umberit M.A. and Sharpless, K.B., J. Am. Chem. Soc., 99, 5526 (1977); de Richter R.K., Bonato M., Follet M. and Kamenka, J-M., J. Org. Chem., 55, 2855 (1990).
25. Ohloff G., Farnow H. and Shade G., Chem. Ber., 89, 1549 (1959); Harwood L.M. and Julia M., Synthesis, 6, 456 (1980); Umberit M.A. and Sharpless, K.B., J. Am. Chem. Soc., 99, 5526 (1977); de Richter R.K., Bonato M., Follet M. and Kamenka, J-M., J. Org. Chem., 55, 2855 (1990).
26. Borowiecki L. and Reca E., Lieb. Ann. Chem., 11, 1 (1974).
27. Peterson P.E. and Grant G., J. Org. Chem., 56, 16 (1991).