An Enantioselective Access to 1-Alkyl-1,2-Dihydroisoquinolines and 1-Alkyl-, 3-Alkyl-, and 1,3-Dialkyl-1,2,3,4-tetrahydroisoquinolines

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1767-1772

  Barbier, Denis ^a   Marazano, Christian ^a   Riche, Claude ^a   Das, Bhupesh C ^a   Potier, Pierre ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003185662     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970768a     Document Type: Article

References (16)

1. Barbier, D.; Marazano, C.; Das, B. C.; Potier, P. J. Org. Chem. 1996, 61, 9596-9598.
2. Génisson, Y.; Marazano, C.; Mehmandoust, M.; Gnecco, D.; Das, B. C. Synlett 1992, 431.
3. For previous results in pyridinium series, see: Génisson, Y.; Marazano, C.; Das, B. C. J. Org. Chem. 1993, 58, 2052.
4. For other examples of the reaction of chiral isoquinolinium salts with Grignard reagents, see: Comins, D. L.; Badawi, M. M. Heterocycles 1991, 32, 1869.
5. For a recent review, see: Rozwadowska, M. D. Heterocycles 1994, 39, 903.
6. Previous enantiospecific accesses to 1,3-disubstituted tetrahydroisoquinolines: (a) Coote, S. J.; Davies, S. G.; Sutton, K. H. J. Chem. Soc., Perkin Trans. 1 1988, 1481. (b) Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 11863. (c) Bringmann, G.; Weirich, R.; Keuscher, H.; Jansen, J. R.; Kisinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877. (d) Tietze, L. F.; Burkhardt, O. Synthesis 1994, 1331. (e) Gosmann, G.; Guillaume, P.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4369.
7. Previous enantiospecific accesses to 1,3-disubstituted tetrahydroisoquinolines: (a) Coote, S. J.; Davies, S. G.; Sutton, K. H. J. Chem. Soc., Perkin Trans. 1 1988, 1481. (b) Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 11863. (c) Bringmann, G.; Weirich, R.; Keuscher, H.; Jansen, J. R.; Kisinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877. (d) Tietze, L. F.; Burkhardt, O. Synthesis 1994, 1331. (e) Gosmann, G.; Guillaume, P.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4369.
8. Previous enantiospecific accesses to 1,3-disubstituted tetrahydroisoquinolines: (a) Coote, S. J.; Davies, S. G.; Sutton, K. H. J. Chem. Soc., Perkin Trans. 1 1988, 1481. (b) Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 11863. (c) Bringmann, G.; Weirich, R.; Keuscher, H.; Jansen, J. R.; Kisinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877. (d) Tietze, L. F.; Burkhardt, O. Synthesis 1994, 1331. (e) Gosmann, G.; Guillaume, P.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4369.
9. Previous enantiospecific accesses to 1,3-disubstituted tetrahydroisoquinolines: (a) Coote, S. J.; Davies, S. G.; Sutton, K. H. J. Chem. Soc., Perkin Trans. 1 1988, 1481. (b) Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 11863. (c) Bringmann, G.; Weirich, R.; Keuscher, H.; Jansen, J. R.; Kisinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877. (d) Tietze, L. F.; Burkhardt, O. Synthesis 1994, 1331. (e) Gosmann, G.; Guillaume, P.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4369.
10. Previous enantiospecific accesses to 1,3-disubstituted tetrahydroisoquinolines: (a) Coote, S. J.; Davies, S. G.; Sutton, K. H. J. Chem. Soc., Perkin Trans. 1 1988, 1481. (b) Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 11863. (c) Bringmann, G.; Weirich, R.; Keuscher, H.; Jansen, J. R.; Kisinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877. (d) Tietze, L. F.; Burkhardt, O. Synthesis 1994, 1331. (e) Gosmann, G.; Guillaume, P.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4369.
11. Yamato, M.; Hashigaki, K.; Qais, N.; Ishikawa, S. Tetrahedron 1990, 46, 5909.
12. Génisson, Y.; Mehmandoust, M.; Marazano, C.; Das, B. C. Heterocycles 1994, 39, 811.
13. For the use of other oxazolidine intermediates in the enantioselective syntheses of 1-alkyl 1,2,3,4-tetrahydroisoquinoline series see references 6e, 7, 8 and Carbonelle, A. C.; Gott, V.; Roussi, G. Heterocycles 1993, 36, 1763.
14. Improved selectivities for the alkylation of related 3,4-dihydroisoquinoline equivalents were observed using benzylic titanium reagents: Hashigaki, K.; Kan, K.; Qais, N.; Takeuchi, Y.; Yamato, M. Chem. Pharm. Bull. 1991, 39, 1126.
15. For a recent review see: Meyers, A. I.; Brengel G. P. Chem. Commun. 1997, 1.
16. Battersby, A. R.; Edwards, T. P. J. Chem. Soc. 1960, 1214.