New entries in Lewis acid-Lewis base bifunctional asymmetric catalyst: Catalytic enantioselective Reissert reaction of pyridine derivatives

Journal of the American Chemical Society

Volumn 126, Issue 38, 2004, Pages 11808-11809

  Ichikawa, Eiko ^a,b   Suzuki, Masato ^a   Yabu, Kazuo ^a   Albert, Matthias ^a   Kanai, Motomu ^a,b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

7 (4 FLUOROPHENOXYMETHYL) 2 (5 FLUORO 2 PYRIMIDINYL) 2,3,4,6,7,8,9,9A OCTAHYDROPYRIDO[1,2 A]PYRAZINE; ALUMINUM; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; ISOQUINOLINE DERIVATIVE; LEWIS ACID; LEWIS BASE; LIGAND; PHOSPHINE OXIDE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DOPAMINERGIC SYSTEM; ENANTIOSELECTIVITY; REISSERT REACTION; SYNTHESIS;

ALUMINUM; CATALYSIS; ISOQUINOLINES; NAPHTHOLS; OXIDES; PHOSPHINES; PIPERIDINES; PYRAZINES; PYRIDINES; PYRIMIDINES; QUINOLINES; STEREOISOMERISM;

EID: 4644272647     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045966f     Document Type: Article

References (28)

1. For recent reviews, see: (a) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
2. (b) Laschat, S.; Dickner, T. Synthesis 2000, 1781.
3. For selected examples, see: (a) Comins, D. L.; Goehring, R. R.; Joseph, S. P.; O'Connor, S. J. Org. Chem. 1990, 55, 2574.
4. (b) Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M.; Normant, J.-F. Synlett 1991, 111.
5. (c) Génisson, Y.; Marazano, C.; Das, B. C. J. Org. Chem. 1993, 58, 2052.
6. (d) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
7. (e) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184.
8. (f) Legault, C.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 6360.
9. (a) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327.
10. (b) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801.
11. (c) Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
12. Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989.
13. Simple pyridine gave the Reissert product in only 25% yield using NaCN as a nucleophile: (a) Reuss, R. H.; Smith, N. G.; Winters, L. J. J. Org. Chem. 1974, 39, 2027.
14. 3: (b) Popp, F. D.; Takeuchi, I.; Kant, J.; Hamada, Y. Chem. Commun. 1987, 1765.
15. 1,4-Adduct was obtained in less than trace amounts in all cases.
16. See Supporting Information for details.
17. We speculated that there is a Lewis base-catalyzed monoactivation pathway of low enantioselectivity for reactive N-acyl pyridinium, due to the higher Lewis basicity of a phosphine oxide than a sulfoxide or a phosphine sulfide.
18. For use of a sulfoxide as a Lewis base activator of TMSCN in a catalytic asymmetric cyanosilylation of aldehydes, see: (a) Rowlands, G. J. Synlett 2003, 236.
19. For recent examples of chiral sulfoxides as Lewis base activators of silicon-containing nucleophiles, see: (b) Rowlands, G. J.; Barnes, W. K. Chem. Commun. 2003, 2712.
20. (c) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610.
21. For an example in which an internal Lewis base stabilizes a highly enantioselective chiral polymetallic complex, see: Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
22. 2-symmetric sulfoxide-containing catalysts 4-Al and 5-Al gave products in 78% yield with 1.3:1 regioselectivity (15 and 1% ee) and in 56% yield with 1:1 regioselectivity (14 and 4% ee), respectively.
23. 3-Al did not give satisfactory results for 7 using neopenryl chloroformate: 1,6-adduct 8d and 1,2-adduct 9d were obtained in 56% yield with 80% ee and 15% yield with 0% ee, respectively.
24. Sanner, M. A.; Chappie, T. A.; Dunaiskis, A. R.; Fliri, A. F.; Desai, K. A.; Zorn, S. H.; Jackson, E. R.; Johnson, C. G.; Morrone, J. M.; Seymour, P. A.; Majchrzak, M. J.; Faraci, W. S.; Collins, J. L.; Duignan, D. B.; Di Prete, C. C.; Lee, J. S.; Trozzi, A. Bioorg. Med. Chem. Lett. 1998, 8, 725.
25. Based on the reaction rate comparison, sulfoxides and phosphine sulfides are weaker activators of TMSCN than phosphine oxides.
26. For Lewis base-catalyzed cyanosilylation of aldehydes, see: (a) Evans, D. A.; Truesdale, L. K. Tetrahedron Lett. 1973, 4929.
27. (b) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537.
28. Relation between enantioselectivity and the A1:6 ratio in the catalyst preparation supported this hypothesis: ee values of lib were 17, 82, 93, and 89% with A1:6 ratios of 1:1.1, 1:1.3, 1:2, and 1:3, respectively.