Lewis acid-mediated nucleophilic alkylations on chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinolines. Asymmetric synthesis of 1-alkyl substituted tetrahydroisoquinolines

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6161-6164

  Yamazaki, Naoki ^a   Suzuki, Hideaki ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; ENANTIOMER; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0030593584     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01337-8     Document Type: Article

References (15)

1. 1. Kametani, T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley & Sons: New York, 1977; Vol. 3, pp 1-272.
2. 2. Rozwadowska, M. D. Heterocycles 1994, 39, 903-931.
3. 3. Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712.
4. 4. N-Acylhydrazonium ions have first described by Speckamp's group in 1988 (Rutjes, F. P. J. T.; Hiemstra, H.; Mooiweer, H. H.; Speckamp, W. N. Tetrahedron Lett. 1988, 29, 6975-6978).
5. 5. Yamato, M.; Hashigaki, K.; Qais, N.; Ishikawa, S. Tetrahedron, 1990, 46, 5909-5920.
6. 6. Retentive selectivity in Grignard alkylation of chiral 4-oxa-7,7a-diazaperhydroindans has been reported: Takahashi, H.; Senda, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 836-842.
7. 7. Maruoka, K.; Yamamoto, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 668-682.
8. 8. Yamamoto, Y.; Sato, H.; Yamada, J. Synlett 1991, 339-341.
9. 9. Amat, M.; Llon, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223-2226.
10. 10. Meyers has published retentive hydride delivery using aluminum hydride reagents to bicyclic lactam having N,O-acetal system: Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656-1662; Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085.
11. 10. Meyers has published retentive hydride delivery using aluminum hydride reagents to bicyclic lactam having N,O-acetal system: Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656-1662; Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085.
12. 11. Battersby, A. R.; Edwards, T. P. J. Chem. Soc. 1960, 1214-1221.
13. 12. Chang, K. C.; Kim, J. K.; Park, C. W. Life Sci. 1992, 52, 67-74.
14. 13. Isolation: Kapadia, G. J.; Shah, N. J.; Highet, R. J. Pharm. Sci. 1964, 53, 1140-1141.
15. 3), has been isolated from Discaria serratifolia: Torres, R.; Monache, F. D.; Bettolo, G. B. M. J. Nat. Prod. 1979, 42, 430-431.