Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 915-919

  Yang, Kung Shuo ^a   Lee, Wei Der ^a   Pan, Jia Fu ^a   Chen, Kwunmin ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL LEWIS ACID;

ACIDITY; AMINES; CATALYSIS; CONDENSATION; DIMERIZATION;

CATALYSTS;

CAMPHOR DERIVATIVE; DIAMINE; HYDRAZINE DERIVATIVE; LEWIS ACID; LIGAND; METAL COMPLEX;

ARTICLE; ASYMMETRIC CATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIMERIZATION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037423177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026318m     Document Type: Article

References (27)

1. For reviews of the Baylis-Hillman reaction, see: (a) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (b) Ciganek, E. Org. React. 1997, 51, 201. (c) Basavaiah, D.; Rao, D. P.; Hyma, R. S. Tetrahedron 1996, 52, 8001. (d) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
2. For reviews of the Baylis-Hillman reaction, see: (a) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (b) Ciganek, E. Org. React. 1997, 51, 201. (c) Basavaiah, D.; Rao, D. P.; Hyma, R. S. Tetrahedron 1996, 52, 8001. (d) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
3. For reviews of the Baylis-Hillman reaction, see: (a) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (b) Ciganek, E. Org. React. 1997, 51, 201. (c) Basavaiah, D.; Rao, D. P.; Hyma, R. S. Tetrahedron 1996, 52, 8001. (d) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
4. For reviews of the Baylis-Hillman reaction, see: (a) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (b) Ciganek, E. Org. React. 1997, 51, 201. (c) Basavaiah, D.; Rao, D. P.; Hyma, R. S. Tetrahedron 1996, 52, 8001. (d) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
5. (a) Kundig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049.
6. (b) Yang, K.-S.; Chen, K. Org. Lett. 2000, 2, 729.
7. (a) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
8. (b) Barrett, A. G. M.; Cook, A. S.; Kamimura, A. J. Chem. Soc. Chem. Commun. 1998, 2533.
9. (c) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1998, 1271.
10. (d) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241.
11. (e) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867.
12. (f) Iwabuchi, Y.; Furukawa, M.; Esumi, T. Hatakeyama, S. Chem. Commun. 2001, 2030.
13. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
14. (a) Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183.
15. (b) Aggarwal, V. K.; Tarver, G. J.; McCague, R. J. Chem. Soc., Chem. Commun. 1996, 2713.
16. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
17. (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
18. (b) Barrett, A. G. M.; Kamimura, A. J. Chem. Soc., Chem Commun. 1995, 1755.
19. (c) Ishihara, K.; Kondo, S.; Yamamoto, H. J. Org. Chem. 2000, 65, 9125.
20. (d) Takasu, M.; Yamamoto, H. Synlett 1990, 194.
21. (e) Sartor, D.; Saffrich, J.; Helmchen, G. Synlett 1990, 197.
22. (f) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611.
23. (g) Pan, J.-F.; Chen, K. J. Mol. Catal. A: Chem. 2001, 176, 19.
24. (h) Yang, K.-S.; Chen, K. Org. Lett. 2002, 4, 1107.
25. Drewes, S. E.; Emslie, N. D.; Field, J. S.; Kahn, A. A.; Ramesar, N. Tetrahedron: Asymmetry 1992, 3, 255.
26. Lee, W.-D.; Yang, K.-S.; Chen, K. Chem. Commun. 2001, 1612.
27. Hahn, F. E.; Mohr, J. Chem. Ber. 1990, 123, 481.