Substituted isoquinolines by Noyori transfer hydrogenation: Enantioselective synthesis of chiral diamines containing an aniline subunit

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6724-6729

  Vedejs, E ^a   Trapencieris, P ^b   Suna, E ^b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 AMINOPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 (2 METHYLAMINOPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; DIAMINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; HYDROGENATION; INHIBITION KINETICS; PROTEIN TRANSPORT; REDUCTION; SYNTHESIS;

EID: 0032885955     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990594s     Document Type: Article

References (22)

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2. (b) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792.
3. Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916. Hashiguchi, S.; Noyori, R. Acc. Chem. Res. 1997, 30, 97.
4. Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916. Hashiguchi, S.; Noyori, R. Acc. Chem. Res. 1997, 30, 97.
5. Ott, H.; Hardtmann, G.; Denzer, M.; Frey, A. J.; Gogerty, J. H.; Leslie, G. H.; Trapold, J. H. J. Med. Chem. 1968, 11, 777.
6. The yellow contaminant could not be separated well enough to give satisfactory analysis or spectra, but one small sample was obtained having a 3:2 ratio of oxygen/nitrogen according to elemental analysis, consistent with structure i, below. Analogous indazole N-oxides are reported as yellow solids: Reissert, A.; Lemmer, F. Chem. Ber. 1926, 59, 351. Behr, L. C. J. Am. Chem. Soc. 1954, 76, 3672. Behr, L. C.; Alley, E. G.; Levand, O. J. Org. Chem. 1962, 27, 65. formula represented
7. The yellow contaminant could not be separated well enough to give satisfactory analysis or spectra, but one small sample was obtained having a 3:2 ratio of oxygen/nitrogen according to elemental analysis, consistent with structure i, below. Analogous indazole N-oxides are reported as yellow solids: Reissert, A.; Lemmer, F. Chem. Ber. 1926, 59, 351. Behr, L. C. J. Am. Chem. Soc. 1954, 76, 3672. Behr, L. C.; Alley, E. G.; Levand, O. J. Org. Chem. 1962, 27, 65. formula represented
8. The yellow contaminant could not be separated well enough to give satisfactory analysis or spectra, but one small sample was obtained having a 3:2 ratio of oxygen/nitrogen according to elemental analysis, consistent with structure i, below. Analogous indazole N-oxides are reported as yellow solids: Reissert, A.; Lemmer, F. Chem. Ber. 1926, 59, 351. Behr, L. C. J. Am. Chem. Soc. 1954, 76, 3672. Behr, L. C.; Alley, E. G.; Levand, O. J. Org. Chem. 1962, 27, 65. formula represented
9. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Datlon Trans, 1 1974, 233.
10. Noyori, R.; Ikariya, T. Personal communication.
11. Vedejs, E.; Kruger, A. W.; Suna, E. Manuscript in preparation.
12. (a) For a recent review on asymmetric reduction of cyclic imines, see: Yurovskaya, M. A.; Karchava, A. V. Tetrahedron: Asymmetry 1998, 3331.
13. (b) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry, 1998, 9, 183. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics, 1998, 17, 3420.
14. (b) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry, 1998, 9, 183. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics, 1998, 17, 3420.
15. (b) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry, 1998, 9, 183. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics, 1998, 17, 3420.
16. (b) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry, 1998, 9, 183. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics, 1998, 17, 3420.
17. (b) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry, 1998, 9, 183. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics, 1998, 17, 3420.
18. (b) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry, 1998, 9, 183. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics, 1998, 17, 3420.
19. We thank Prof. Noyori for informing us of this result and for providing a sample of catalyst 5-Nps.
20. The chloro analogue of 20a was reduced with promising ee (catalyst 5-Ts: 66% yield, 91% ee; catalyst 5-Nps: 56% yield, 86% ee), but the amine displacement was not attempted.
21. The copper-catalyzed animations give lower yields with larger n-alkylamines; for example, N,N-dimethylethylenediamine afforded 30% of the displacement product under the usual conditions.
22. 3 (41.9 mL, 0.3M) and distillation of the resulting mixture in vacuo (aspirator, 15 mmHg, collected fractions bp: 91-92°C, bath temperature 155-160°C); see: Narita, K.; Sekiya, M. Chem. Pharm. Bull. 1977, 25, 135.