Asymmetric Reissert-type reaction promoted by bifunctional catalyst [21]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6327-6328

  Takamura, Masahiro ^a   Funabashi, Ken ^a   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENANTIOMER; LETTER; MOLECULAR MODEL; REACTION ANALYSIS;

EID: 0034608930     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0010352     Document Type: Letter

References (23)

1. (a) Reissert, A. Chem. Ber. 1905, 38, 1603.
2. (b) For Lewis acid-catalyzed Reissert-type reaction using TMSCN, see: Ruchirawat, S.; Phadungkul, N.; Chuankamnerdkarn, M.; Thebtaranonth, C. Heterocycles 1977, 6, 43-46.
3. (a) Popp, F. D. Heterocycles 1973, 1, 165-180.
4. (b) McEwen, W. E.; Cobb, R. L. Chem. Rev. 1955, 55, 511-549.
5. (a) Lorsbach, B. A.; Bagdanoff, J. T.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1998, 63, 2244-2250.
6. (b) Lorsbach, B. A.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
7. (a) Leeson, P. D.; Carling, R. W.; Moore, K. W.; Moseley, A. M.; Smith, J. D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954-1968.
8. (b) Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Tamiki, N.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M. J. Med. Chem. 1994, 37, 3956-3968.
9. Chiral tetrahydroquinoline-2-carboxylate 9 has only been available by the resolution of the racemic compound: (a) Paradisi, M. P.; Romeo, A. J. Chem. Soc. Perkin Trans 1 1976, 596-600. (b) Katayama, S.; Ae, N.; Nagata, R. Tetrahedron: Asymmetry 1998, 9, 4295-4299.
10. Chiral tetrahydroquinoline-2-carboxylate 9 has only been available by the resolution of the racemic compound: (a) Paradisi, M. P.; Romeo, A. J. Chem. Soc. Perkin Trans 1 1976, 596-600. (b) Katayama, S.; Ae, N.; Nagata, R. Tetrahedron: Asymmetry 1998, 9, 4295-4299.
11. To the best of our knowledge, even diastereoselective reactions using chiral acid chlorides have not been reported.
12. For determination of the reactive acyl quinolinium ion intermediate of a Reissert-type reaction, see: (a) Duane, F. F.; Popp, F. D. J. Hetenicycl. Chem. 1991, 28, 1801-1804. (b) Abushanab, E.; Lee, D.-Y. J. Org. Chem. 1975, 40, 3376-3378. (c) Akiba, K.; Negishi, Y.; Inamoto, N. Synthesis 1979, 55-57.
13. For determination of the reactive acyl quinolinium ion intermediate of a Reissert-type reaction, see: (a) Duane, F. F.; Popp, F. D. J. Hetenicycl. Chem. 1991, 28, 1801-1804. (b) Abushanab, E.; Lee, D.-Y. J. Org. Chem. 1975, 40, 3376-3378. (c) Akiba, K.; Negishi, Y.; Inamoto, N. Synthesis 1979, 55-57.
14. For determination of the reactive acyl quinolinium ion intermediate of a Reissert-type reaction, see: (a) Duane, F. F.; Popp, F. D. J. Hetenicycl. Chem. 1991, 28, 1801-1804. (b) Abushanab, E.; Lee, D.-Y. J. Org. Chem. 1975, 40, 3376-3378. (c) Akiba, K.; Negishi, Y.; Inamoto, N. Synthesis 1979, 55-57.
15. 2AlCl, peaks corresponding to the adduct of TMSCN to 1a were not observed in the absence of acid halides. In addition, as will be mentioned in ref 13, addition of TMSCN is not the major rate-determining step, which may not be consistent with the mechanism involving the direct attack of cyanide to quinoline. Consequently, it appears, at the moment, that the reaction would proceed via an acyl quinolinium intermediate.
16. (a) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Six 1999, 121, 2641-2642.
17. (b) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 1650-1652.
18. No acylated or silylated ligand was observed by TLC analysis.
19. Longer reaction lime did not improve the chemical yield.
20. For the strategy to restrict the conformation of the ligand for the dual activation pathway, see: Kanai, M.; Hamashima, Y.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 2405-2409.
21. The major rate-determining step would be the formation of the acyl quinolinium ion. However, the cyanation step was found to have some contribution to the reaction rate. Kinetic studies indicated that the total reaction rate was 0.2 order with respect to TMSCN. See Supporting Information.
22. 3 was added. Usual workup and purification by silica gel column chromatography (AcOEt/hexane, 3/7) gave the product in 99% yield. The ee was determined to be 91% by chiral HPLC analysis (DAICEL CHRALPAK AS, 'PrOH/hexane, 3/7, How = 1.0 mL/min, retention time, 15.7 min (major), 20.8 min (minor)).
23. 2-toluene mixed solvent with 5 gave less satisfactory results (32, 48, and 59% ee's, respectively).