Asymmetric transformation of chiral auxiliary-substituted N-acyl-α-dehydro(1-naphthyl)alanines into 3,4-dihydrobenzo[f]quinolinone derivatives via photoinduced electron transfer

Tetrahedron

Volumn 60, Issue 5, 2004, Pages 1183-1189

  Maekawa, Kei ^a   Kubo, Kanji ^b   Igarashi, Tetsutaro ^a   Sakurai, Tadamitsu ^a  

^a KANAGAWA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

Amino acids and derivatives; Asymmetric induction; Dihydrobenzoquinolinones; Electron transfer; Photochemistry

Indexed keywords

2 ACETYLAMINO 3,4 DIHYDRO 1 [1 (METHOXYCARBONYL)ETHYL] 2(1H) BENZO[F]QUINOLINONE; 2 ACETYLAMINO N [1 (METHOXYCARBONYL)ETHYL] 3 (1 NAPHTHYL) 2 PROPENAMIDE; 2 BENZOYLAMINO 3,4 DIHYDRO 1 [1 (METHOXYCARBONYL)ETHYL] 2(1H) BENZO[F]QUINOLINONE; 2 BENZOYLAMINO N [1 (METHOXYCARBONYL)ETHYL] 3 (1 NAPHTHYL) 2 PROPENAMIDE; 2 [1 (METHOXYCARBONYL)ETHYLAMINOCARBONYL] 4 METHYLBENZ[F]ISOQUINOLINE; ALANINE DERIVATIVE; AMIDE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ELECTRON TRANSPORT; PHOTOCHEMISTRY; PRIORITY JOURNAL; TEMPERATURE SENSITIVITY;

EID: 0346339564     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.071     Document Type: Article

References (39)

1. Horspool W.M. Synthetic Organic Photochemistry. 1984;Plenum, New York.
2. Rau H. Chem. Rev. 83:1983;535-547.
3. Koch H., Runsink J., Scharf H.-D. Tetrahedron Lett. 24:1983;3217-3220.
4. Naito T., Toda Y., Ninomiya I. Heterocycles. 22:1984;237-240.
5. Lange G.L., Decicco C., Lee M. Tetrahedron Lett. 28:1987;2833-2836.
6. Rao V.P., Turro N.J. Tetrahedron Lett. 30:1989;4641-4644.
7. Piva O., Mortezaei R., Henin F., Muzart J., Pete J.-P. J. Am. Chem. Soc. 112:1990;9263-9284.
8. Piva O., Pete J.-P. Tetrahedron Lett. 31:1990;5157-5160.
9. Inoue Y. Chem. Rev. 92:1992;741-770.
10. Christoph H., Xuechao X., Warzecha K.-D., Peter R., Helmunt G., Martin D. Pure Appl. Chem. 70:1998;2167-2176.
11. Jayaraman S., Uppili S., Natarajan A., Joy A., Chong K.C.W., Netherton M.R., Zenova A., Scheffer J.R., Ramamurthy V. Tetrahedron Lett. 41:2000;8231-8235.
12. Kohmoto S., Miyaji Y., Tsuruoka M., Kishikawa K., Yamamoto M., Yamada K. J. Chem. Soc. Perkin Trans. 1. 2001;2082-2088.
13. Formentin P., Sabater M.J., Chretien M.N., Garcia H., Scaiano J.C.J. J. Chem. Soc. Perkin Trans. 2. 2002;164-167.
14. Shim S.C., Kim D.S., Yoo D.J., Wada T., Inoue Y. J. Org. Chem. 67:2002;5718-5726.
15. Leibovitch M., Olovsson G., Sundarababu G., Ramamurthy V., Scheffer J.R. J. Am. Chem. Soc. 118:1996;1219-1220.
16. Gamlin J.N., Jones R., Lelbovitch M., Patrick B., Scheffer J.R., Trotter J. Acc. Chem. Res. 29:1996;203-209.
17. Mordechai L., Gunnar O., John R.S., James T. J. Am. Chem. Soc. 120:1998;12755-12769.
18. Joy A., Scheffer J.R., Ramamurthy V. Org. Lett. 2:2000;119-121.
19. Scheffer J.R. Can. J. Chem. 79:2001;349-357.
20. Shailaja J., Sundararajan U., Joy A., Ramamurthy V. Microporous Mesoporous Mater. 48:2001;319-328.
21. Kaanumalle L.S., Sivaguru J., Arunkumar N., Karthikeyan S., Ramamurthy V. Chem. Commun. 2003;116-117.
22. Bertrand S., Hoffmann N., Humbel S., Pete J. J. Org. Chem. 65:2000;8690-8703.
23. Griesbeck A.G., Kramer W., Lex J. Angew. Chem. Int. Ed. 40:2001;577-579.
24. Jones S., Atherton J.C.C. Tetrahedron: Asymmetry. 12:2001;1117-1119.
25. Bach T., Bergmann H., Grosch B., Harms K. J. Am. Chem. Soc. 124:2002;7982-7990.
26. Chong K.C.W., Sivaguru J., Shichi T., Yoshimi Y., Ramamurthy V., Scheffer J.R. J. Am. Chem. Soc. 124:2002;2858-2859.
27. Sakurai T., Morioka Y., Maekawa K., Kubo K. Heterocycles. 53:2000;271-276.
28. Maekawa K., Igarashi T., Kubo K., Sakurai T. Tetrahedron. 57:2001;5515-5526.
29. Martinez G.R., Walker K.A.M., Hirschfeld D.R., Bruno J.J., Yang D.S. J. Med. Chem. 35:1992;620-628.
30. Jones C.D., Audia J.E., Lawhorn D.E., McQuaid L.A., Neubauer B.L., Pike A.J., Pennington P.A., Stamm N.B., Toomey R.E., Hirsch K.S. J. Med. Chem. 36:1993;421-423.
31. Nishikawa T., Omura M., Iizuka T., Saito I., Yoshida S. Arzneim.-Forsch./Drug Res. 46:1996;875-878.
32. Oshiro Y., Sato S., Kurahashi N., Tanaka T., Kikuchi T., Tottori K., Uwahodo Y., Nishi T. J. Med. Chem. 41:1998;658-667.
33. Oshiro Y., Sakurai Y., Sato S., Kurahashi N., Tanaka T., Kikuchi T., Tottorii K., Uwahodo Y., Miwa T., Nishi T. J. Med. Chem. 43:2000;177-189.
34. Butenschön I., Möller K., Hönsel W. J. Med. Chem. 44:2001;1249-1256.
35. Rao Y.S., Filler R. Synthesis. 1975;749-764.
36. Rzeszotarska B., Karolak-Wojciechowska J., Broda M.A., Galdecki Z., Trzezwinska B., Koziol A.E., Int J. Int. J. Pept. Protein Res. 44:1994;313-319.
37. Molecular Structure Corporation, teXan for Windows. Single Crystal Structure Analysis Software. Ver. 1.06; The Woodlands: Texas, 1999.
38. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A. J. Appl. Cryst. 27:1994;1045-1050.
39. Sheldrick G.M. Program for the refinement of crystal structure. SHELXL 97. 1997;University of Gottingen, Gottingen.