Enantioselective Pictet-Spengler Reaction of Nitrones Derived from Nb-Hydroxytryptamine with Aldehydes Catalyzed by Chiral Brønsted Acid-Assisted Lewis Acids

Synlett

Volumn 1997, Issue 7, 1997, Pages 761-762

  Kawate, Tomohiko ^a   Yamada, Hideki ^a   Matsumizu, Miyako ^a   Nishida, Atsushi ^a   Nakagawa, Masako ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001373649     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5784     Document Type: Article

References (13)

1. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
2. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
3. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
4. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
5. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
6. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
7. Reviews of the Pictet-Spengler reaction: (a) Whaley, W. M.; Govindachari, T. R. 'Organic Reactions', vol 6, p151, 1951, John Wiley & Sons; (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797; (c) Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402-2403; (d) Schmidt, G.; Waldmann, H.; Henke, H.; Burkard, M. Chem. Eur. J., 1996, 2, 1566-1571; Typical application to natural product synthesis; (e) Hino, T.; Nakagawa, M. J. Heterocyclic Chem. 1994, 31, 625 and references cited therein; (f) Nakagawa, M.; Liu, J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721; (g) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron, 1988, 44, 359.
8. (a) Than Soe; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles, 1996, 42, 347-358;
9. (b) Than Soe; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M, Tetrahedron Lett., 1995, 36, 1857-1860;
10. (c) Kawate, T.; Yamada, H.; Than Soe; Nakagawa, M. Tetrahedron: Asymmetry, 1996, 7, 1249;
11. (d) Kawate, T.; Yamada, H.; Matsumizu, M.; Nishida, A.; Nakagawa, M. manuscript in preparation.
12. Ishihara, K.; Miyata, M.; Hattori, K.; Toda, T.; Yamamoto, H. J. Am. Chem. Soc., 1994, 116, 10520.
13. 4. Evaporation of the solvent gave a yellow solid, which was chromatographed on silica gel with AcOEt/ n-hexane (1/6∼ 1/2 ∼ 1/0) to give the hydroxytetrahydro-β-carboline 2a (85.7 mg, 82%) as a colorless solid, 2, 2′-Dihydroxy-1, 1′-binaphthyl (S)-3 (436.0 mg) and the nitrone 1a (6.8 mg, 6.5%) were recovered. The enantiomeric excess of 2a (78% ee, R) was determined by a chiral HPLC analysis, using Daicel Chiralcel-OD (eluent: n-hexane/ isopropanol 90/10, flow rate: 1.0 ml/min).