Enantioresolution by the chiral phthalic acid method: Absolute configurations of (2-methylphenyl)phenylmethanol and related compounds

Tetrahedron Asymmetry

Volumn 10, Issue 11, 1999, Pages 2075-2078

  Watanabe, Masataka ^a   Kuwahara, Shunsuke ^a   Harada, Nobuyuki ^a   Koizumi, Masatoshi ^b   Ohkuma, Takeshi ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL DERIVATIVE; PHTHALIC ACID;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033522731     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00231-1     Document Type: Article

References (21)

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2. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
3. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
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5. (a) Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc. 1993, 115, 7547.
6. (b) Harada, N.; Nehira, T.; Soutome, T.; Hiyoshi, H.; Kido, F. Enantiomer 1996, 1, 35.
7. (c) See also: Toyota, S.; Yasutomi, A.; Oki, M. Tetrahedron Lett. 1995, 36, 6297.
8. (a) Harada, N.; Koumura, N.; Robillard, M. Enantiomer 1997, 2, 303.
9. (b) Harada, N.; Hiyoshi, N.; Vassilev, V. P.; Hayashi, T. Chirality 1997, 9, 623.
10. (c) Harada, N.; Vassilev, V. P.; Hiyoshi, N. Enantiomer 1997, 2, 123.
11. (d) Nemoto, H.; Miyata, J.; Fukumoto, K.; Ehara, H.; Harada, N.; Uekusa, H.; Ohashi, Y. Enantiomer 1997, 2, 127.
12. (e) Harada, N.; Koumura, N.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 7256.
13. (f) Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1997, 2, 359.
14. (g) Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1998, 3, 64.
15. (h) Kuwahara, S.; Fujita, K.; Watanabe, M.; Harada, N.; Ishida, T. Enantiomer, 1999, 4, in press.
16. Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Ikariya, T.; Noyori, R. in preparation.
17. Cervinka, O.; Suchan, V.; Masak, B. Collect. Czech. Chem. Commun. 1965, 30, 1693. Cervinka, O.; Belovsky, O.; Fabryova, A.; Dudek, V.; Grohman, K. Collect. Czech. Chem. Commun. 1967, 32, 2618.
18. Cervinka, O.; Suchan, V.; Masak, B. Collect. Czech. Chem. Commun. 1965, 30, 1693. Cervinka, O.; Belovsky, O.; Fabryova, A.; Dudek, V.; Grohman, K. Collect. Czech. Chem. Commun. 1967, 32, 2618.
19. 2 respectively. Since the reported value in benzene is very small, we recommend the use of chloroform or ethanol instead of benzene.
20. D measurement: Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H.; Okamoto, Y.; Yuki, H.; Kawada, Y. J. Chem. Soc., Perkin Trans. 1 1985, 1845. Harada, N. Enantiomer 1996, 1, 81.
21. D measurement: Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H.; Okamoto, Y.; Yuki, H.; Kawada, Y. J. Chem. Soc., Perkin Trans. 1 1985, 1845. Harada, N. Enantiomer 1996, 1, 81.