β-isocupreidine-catalyzed Baylis-Hillman reaction of chiral N-Boc-α-amino aldehydes

Organic Letters

Volumn 8, Issue 23, 2006, Pages 5357-5360

  Nakano, Ayako ^a   Takahashi, Keisuke ^a   Ishihara, Jun ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BETA ISOCUPREIDINE; BETA-ISOCUPREIDINE; HETEROCYCLIC COMPOUND; QUINOLINOL DERIVATIVE; QUINUCLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ALDEHYDES; HETEROCYCLIC COMPOUNDS; HYDROXYQUINOLINES; MOLECULAR STRUCTURE; QUINUCLIDINES;

EID: 33845270124     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0622561     Document Type: Article

References (30)

1. For reviews, see: (a) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035-1050.
2. (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-892.
3. (c) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4-16.
4. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049-3052.
5. (e) Ciganek, E. Org. React. 1997, 51, 201-350.
6. (f) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062.
7. Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670.
8. (a) Ameer, F.; Drewes, S. E.; Houston-McMillan, M. S.; Kaye, P. T. S. Afr. J. Chem. 1986, 39, 57-62.
9. (b) Roos, G.; Manickum, T. Synth. Commun. 1991, 21, 2269-2274.
10. (c) Drewes, S. E.; Khan, A. A.; Rowland, K. Synth. Commun. 1993, 23, 183-188.
11. (d) Manickum, T.; Roos, G. H. P. S. Afr. J. Chem. 1994. 47, 1-16.
12. (e) Nayak, S. P.; Thijs, L.; Zwanenburg Tetrahedron Lett. 1999, 40, 981-9984.
13. (f) Almeida, B. W. P.; Coelho, F. Tetrahedron Lett. 2003, 44, 937-940.
14. Coelho, F.; Diaz, G.; Abella, C. A. M.; Almeida, W. P. Synlett 2006, 435-439.
15. Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867-7871.
16. (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 127, 10219-10220.
17. (b) Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030-3031.
18. (c) Kawahara, S.; Nakano, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 3103-3105.
19. (d) Nakano, A.; Kawahara, S.; Akamatsu, S.; Morokuma, K.; Nakatani, M.; Iwabuchi, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Tetrahedron 2006, 62, 381-389.
20. 4 reduction followed by benzoylation.
21. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709.
22. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364.
23. 13C NMR data provided by Professor F. Coelho.
24. Dondoni, A.; Fantin, G.; Fagagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446.
25. 5d
26. This ElcB process is assumed to involve a six-membered proton transfer from the phenolic OH to the alkoxide of zwitterionic intermediate 10 or 11 with concomitant deprotonation of the α-methine to give an enolate, followed by elimination of β-ICD via 12 as proposed by Aggarwal et al. Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem. Int. Ed. 2005, 44, 1706-1708.
27. For recent reports on the reaction mechanism see ref 12 and: (a) Santos, L. S.; Pavam, W. P.; Coelho, F.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 4330-4333.
28. (b) Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147-150.
29. (c) Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980-3987.
30. (d) Buskens, P.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2005, 127, 16762-16763.