Novel asymmetric C-C bond formation process promoted by Et2AlCl and its application to the stereoselective synthesis of unusual β-branched Baylis- Hillman adducts

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 1061-1064

  Li, Guigen ^a   Wei, Han Xun ^a   Whittlesey, Bruce R ^a   Batrice, Nassim N ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM CHLORIDE; COPPER DERIVATIVE; ETHANE; TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033524893     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981976l     Document Type: Article

References (44)

1. (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
2. (b) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
3. Ciganek, E. Org. React. 1997, 51, 201.
4. Brzezinski, L. J.; Rafel, S.; Leahy, J. M. J. Am. Chem. Soc. 1997, 119, 4317.
5. Marko, I. E.; Giles, P. G.; Hindley, N. J. Tetrahedron 1997, 53, 1015.
6. Aggarwal, V.; Tarver, G. J.; McCague, R. J. Chem. Soc. Chem. Commun. 1996, 2713.
7. (a) Genisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem. Soc., Perkin Trans. 1 1996, 2860.
8. (b) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 36, 6495-6498.
9. (c) Dennis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Jost, P.; Greene, A. E. J. Chem. Soc., Perkin Trans. 1 1995, 1811.
10. (a) Xu, L.-H.; Kundig, E. P. Helv. Chim. Acta 1994, 77, 1480.
11. (b) Kundig, E. P.; Xu, L.-H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049.
12. (c) Kundig, E. P.; Xu, L.-H.; Schnell, B. Synlett 1994, 413.
13. (a) Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org. Chem. 1988, 53, 1037.
14. (b) Tsuda, T.; Yoshida, T.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1987, 52, 1624.
15. (a) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
16. (b) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621.
17. (a) Li, G.; Wei, H.-X.; Willis, S. Tetrahedron Lett. 1998, 39, 4607.
18. (b) Wei, H.-X.; Willis, S.; Li, G. Synth. Commun. accepted
19. (c) Li, G.; Wei, H.-X.; Willis, S. Tetrahedron Lett. 1998, 39, 8203.
20. (d) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Alaniz, J. R. de Tetrahedron Lett. 1998, 39, 8791.
21. (e) Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428.
22. Corey, E. J.; Katzenellebogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851.
23. Siddall, J. B.; Biskup, M.; Fried, J. H. J. Am. Chem. Soc. 1969, 91, 1853. For recent reviews about organocopper reagents, see refs 13-16.
24. Lipshutz, B. H. in Comprehensive Organic Synthesis Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 107-138.
25. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
26. Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277.
27. Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 187.
28. Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13 and refereces therein.
29. Liu, G.-C.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
30. (a) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. H. J. Org. Chem. 1996, 61, 441.
31. (b) Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4.
32. (c) Davis, F. A.; Reddy, T. R.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387.
33. (d) Hua, D. H.; Lagneau, N.; Wang, H.; Chen, J. Tetrahedron: Asymmetry 1995, 6, 349.
34. Davis, F. A.; Zhou, P.; Reddy, V. G. J. Org. Chem. 1994, 58, 3243.
35. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.-M.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
36. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
37. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810.
38. (c) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649.
39. (d) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813.
40. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, S. V.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
41. (b) Martin, S. V.; Nunez, M. T. J. Org. Chem. 1990, 55, 1928.
42. Brook, M. A.; Chan, T. H. Synthesis 1983, 201.
43. -1, 11.57 min (S), 12.42 min (R). Some racemization was observed in these two oxidation procedures.
44. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.