Highly diastereoselective synthesis of new optically active aminoalcohols in one step from (+)-camphor and (-)-fenchone

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1869-1876

  Genov, Miroslav ^a   Kostova, Kalina ^a   Dimitrov, Vladimir ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CAMPHOR; KETONE; ORGANOLITHIUM COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0030920627     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00182-1     Document Type: Article

References (27)

1. Reviews: (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34.
2. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
3. (c) Blaser, H.-U. Chem. Rev. 1992, 92, 935, presents a comprehensive list of ligands.
4. (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
5. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597.
6. (c) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
7. (d) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19.
8. (e) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832.
9. (f) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327.
10. (g) Kitamura, M.; Yamakawa, M.; Oka, H.; Noyori, R. Chem. Eur. J. 1996, 2, 1173.
11. (a) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645.
12. (b) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777.
13. Chelucci, G.; Soccolini, F. Tetrahedron: Asymmetry 1992, 3, 1235.
14. (a) Dimitrov, V.; Bratovanov, S.; Simova, S.; Kostova, K. Tetrahedron Lett. 1994, 35, 6713.
15. (b) Dimitrov, V.; Simova, S.; Kostova, K. Tetrahedron 1996, 52, 1699.
16. (c) Dimitrov, V.; Kostova, K.; Hesse, M. Tetrahedron: Asymmetry 1994, 5, 1891.
17. (d) Dimitrov, V.; Genov, M.; Simova, S.; Linden, A. J. Organomet. Chem. 1996, 525, 213.
18. (e) Dimitrov, V.; Philipova, I.; Simova, S. Tetrahedron: Asymmetry 1996, 7, 1493.
19. Dimitrov, V.; Kostova, K.; Genov, M. Tetrahedron Lett. 1996, 37, 6787.
20. Thiele, K.-H.; Langguth, E.; Müller, G. E. Z. anorg. allg. Chem. 1980, 462, 152.
21. Brandsma, L.; Verkruijsse, H. D. Preparative Polar Organometallic Chemistry, Vol. 1; Springer-Verlag: Berlin Heidelberg, 1987; pp. 114-213.
22. Chadwick, D. J.; Willbe, C. J. Chem. Soc., Perkin I, 1977, 887.
23. 1H NMR spectrum.
24. Lepley, A. R.; Khan, W. A.; Giumanini, A. B.; Giumanini, A. G. J. Org. Chem. 1966, 31, 2047.
25. 4). After evaporation of the solvent the residue was distilled or chromatographed to afford pure 1-phenyl-1-propanol.
26. 4 is somewhat confusing, showing an absolute configuration 1S for the camphor skeleton.
27. 20=+45.4 (c=2.0, EtOH).