Preparation of optically active 8,8′-disubstituted 1,1′-biisoquinoline

Heterocycles

Volumn 42, Issue 1, 1996, Pages 415-422

  Hirao, Ken Ichi ^a   Tsuchiya, Ryuta ^a   Yano, Yasuhiro ^a   Tsue, Hirohito ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001496178     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S60     Document Type: Article

References (15)

1. Cf. T. Hattori, N. Koike, and S. Miyano, J. Chem. Soc., Perkin Trans. 1, 1994, 2273; D. Lew and I. Amer, Tetrahedron Asymm., 1993, 4, 2147; E. Weber, K. Skobridis, A. Wierig, S. Stathi, L. R. Nassimbeni, and M. L. Niven, Angew. Chem., Int . Ed. Engl., 1993, 32, 606.
2. Cf. T. Hattori, N. Koike, and S. Miyano, J. Chem. Soc., Perkin Trans. 1, 1994, 2273; D. Lew and I. Amer, Tetrahedron Asymm., 1993, 4, 2147; E. Weber, K. Skobridis, A. Wierig, S. Stathi, L. R. Nassimbeni, and M. L. Niven, Angew. Chem., Int . Ed. Engl., 1993, 32, 606.
3. Cf. T. Hattori, N. Koike, and S. Miyano, J. Chem. Soc., Perkin Trans. 1, 1994, 2273; D. Lew and I. Amer, Tetrahedron Asymm., 1993, 4, 2147; E. Weber, K. Skobridis, A. Wierig, S. Stathi, L. R. Nassimbeni, and M. L. Niven, Angew. Chem., Int . Ed. Engl., 1993, 32, 606.
4. Cf. A. Sitlani, C. M. Dupureur, and T. K. Barton, J. Am. Chem. Soc., 1993, 115, 12589; J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1990, 29, 1304.
5. Cf. A. Sitlani, C. M. Dupureur, and T. K. Barton, J. Am. Chem. Soc., 1993, 115, 12589; J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1990, 29, 1304.
6. M. Crawford and I. F. B. Smyth, J. Chem. Soc., 1954, 3464.
7. D. M. Bailey, C. G. Degrazia, H. E. Lape, R. Frering, D. Fort, and T. Skulan, J. Med. Chem., 1973, 16, 151.
8. Y. Nagao, T. Marumo, Y. Abe, and T. Misono, Nippon Kagaku Kaishi, 1988, 101.
9. M. Tiecco. L. Testaferri, M. Tingoli, D. Chanelli, and M. Montanucci, Synthesis, 1987, 736.
10. J. B. Hendrickson and C. Rodríguez, J. Org. Chem., 1983, 48, 3344.
11. M. M. Robinson and B. L. Robinson, J. Org. Chem., 1957, 21, 1337.
12. D. Dirnberger and W. Wiegreke, Arch. Pharm., 1990, 323.
13. All attempts to resolve dimethoxy-biisoquinoline (2b) were unsuccessful, whereas resolution of N, N'-dioxide of 2b was achieved by hplc on the RU-1 column. Studies on reduction of N-oxide groups to aromatic amines without racemization are now in progress.
14. This is the first example of the resolution of chiral 1,1′-biisoquinoline nucleus. Recently, optical resolution of 1,1′-biisoquinoline-N,N'-dioxide was reported (M. Fujii and A. Honda, J. Heterocycl. Chem., 1992, 29, 931), and optically active 7,7′ - dimethoxy - 8,8′ - biisoquinoline was also prepared ( K. Yamamoto, K. Watanabe, H. Chikamatsu, Y. Okamoto, and T. Yoshida, J. Chem. Soc., Chem. Commun., 1987, 807). However, these examples are equivalent to 1,1′ - binaphthalene from the standpoint of stereochemistry.
15. This is the first example of the resolution of chiral 1,1′-biisoquinoline nucleus. Recently, optical resolution of 1,1′-biisoquinoline-N,N'-dioxide was reported (M. Fujii and A. Honda, J. Heterocycl. Chem., 1992, 29, 931), and optically active 7,7′ - dimethoxy - 8,8′ - biisoquinoline was also prepared ( K. Yamamoto, K. Watanabe, H. Chikamatsu, Y. Okamoto, and T. Yoshida, J. Chem. Soc., Chem. Commun., 1987, 807). However, these examples are equivalent to 1,1′ - binaphthalene from the standpoint of stereochemistry.