An efficient synthetic approach to optically active β-carboline derivatives via Pictet-Spengler reaction promoted by trimethylchlorosilane

Tetrahedron Asymmetry

Volumn 14, Issue 2, 2003, Pages 177-180

  Tsuji, Riichiro ^a   Nakagawa, Masako ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BETA CARBOLINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CHLOROTRIMETHYLSILANE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PICTET SPENGLER REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037449666     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00793-0     Document Type: Article

References (27)

1. Whaley W.M., Govindachari T.R. Organic Reactions. 6:1951;151-206 Wiley, New York.
2. Cox E.D., Cook J.M. Chem. Rev. 95:1995;1797-1842.
3. Nakagawa M., Kodato S., Hongu M., Kawate T., Hino T. Tetrahedron Lett. 27:1986;6217-6220.
4. Kodato S., Nakagawa M., Kawate T., Hino T. Tetrahedron. 44:1988;359-377.
5. Hino T., Kawate T., Nakagawa M. Tetrahedron. 45:1989;1941-1944.
6. Nakagawa M., Liu J., Hino T. J. Am. Chem. Soc. 111:1989;2721-2722.
7. Nakagawa M., Liu J., Hino T., Tsuruoka A., Harada N., Ariga M., Asada Y. J. Chem. Soc., Perkin Trans. 1. 2000;3477-3486.
8. Liu J., Hino T., Tsuruoka A., Harada N., Nakagawa M. J. Chem. Soc., Perkin Trans. 1. 2000;3487-3494.
9. Kawate T., Yamada H., Soe T., Nakagawa M. Tetrahedron Asymmetry. 7:1996;1249-1252.
10. Kawate T., Yamada H., Matsumizu M., Nishida A., Nakagawa M. Synlett. 7:1997;761-762.
11. Yamada H., Kawate T., Matsumizu M., Nishida A., Nakagawa M. J. Org. Chem. 63:1998;6348-6354.
12. Tsuji R., Yamanaka M., Nishida A., Nakagawa M. Chem. Lett. 2002;428-429.
13. Soe T., Kawate T., Fukui N., Hino T., Nakagawa M. Heterocycles. 42:1996;347-358.
14. Kawate T., Yamanaka M., Nakagawa M. Heterocycles. 50:1999;1033-1038.
15. Waldmann H., Schmidt G., Jansen M., Geb J. Tetrahedron Lett. 34:1993;5867-5870.
16. Waldmann H., Schmidt G. Tetrahedron. 50:1994;11865-11884.
17. Waldmann H., Schmidt G., Henke H., Burkard M. Angew. Chem., Int. Ed. Engl. 34:1995;2402-2403. and references cited therein.
18. Gremmen C., Willemse B., Wanner M.J., Koomen G.-J. Org. Lett. 2:2000;1955-1958.
19. 2-promoted side reactions.
20. Comins D.L., Badawi M.M. Tetrahedron Lett. 26:1991;2995-2996.
21. Comins D.L., Thakker P.M., Baevsky M.F., Badawi M.M. Tetrahedron. 53:1997;16327-16339.
22. Deprotection of the TBS group of β-carbolines was observed under these conditions.
23. 4. Removal of solvent in vacuo gave a residue which was purified by column chromatography (silica gel, 8:1 n-hex/AcOEt) to give 4b as a mixture of diastereomers (105 mg, 89%, 80% d.e.). Diastereomeric excess was determined by HPLC [DAICEL CHIRALCEL OD, hexane:iPrOH=95:5, flow rate: 2.0 mL/min, retention time: 4.1 min (minor) and 7.2 min (major)].
24. Akimoto H., Okamura K., Yui M., Shioiri T., Kuramoto M., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 11:1974;2614-2623.
25. Shiqi P., Min G., Winterfeldt E. Liebigs Ann. Chem. 1993;137-140.
26. Potin D., Dumas F. Synth. Commun. 20:1990;2805-2813.
27. Ort O. Org. Synth. Coll. VIII. 1993;522.