TMSOTf-catalyzed stereoselective isomerization of acetates of the Baylis-Hillman adducts

Synthesis

Volumn , Issue 4, 2000, Pages 545-548

  Basavaiah, Deevi ^a   Muthukumaran, Kannan ^a   Sreenivasulu, Bandaru ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

1,2 interaction; Baylis Hillman reaction; Isomerization; Stereoselectivity; Trimethylsilyl trifluoromethanesulfonate

Indexed keywords

ACETIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034115468     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6372     Document Type: Article

References (27)

1. Ihara, M.; Suzuki, S.; Taniguchi, N.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1993, 755.
2. Oishi, M.; Aratake, S.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 8271.
3. Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. Chem. Commun. 1996, 2625.
4. Kobayashi, M.; Masumoto, K.; Nakai, E.; Nakai, T. Tetrahedron Lett. 1996, 37, 3005.
5. Hunter, R.; Michael, J. P.; Tomlinson, G. D. Tetrahedron 1994, 50, 871.
6. Fujii, N.; Otaka, A.; Ikemura, O.; Akaji, K.; Funakoshi, S.; Hayashi, Y.; Kuroda, Y.; Yajima, H. J. Chem. Soc., Chem. Commun. 1987, 274.
7. Ciganek, E. In Organic Reactions, Vol. 51; Paquette, L. A., Ed.; Wiley: New York, 1997; pp 201-350.
8. Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001.
9. Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
10. Chamakh, A.; Amri, H. Tetrahedron Lett. 1998, 39, 375.
11. Matsumoto, S.; Okubo, Y.; Mikami, K. J. Am. Chem. Soc. 1998, 120, 4015.
12. Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183.
13. Barrett, A. G. M.; Cook, A. S.; Kamimura, A. Chem. Commun. 1998, 2533.
14. Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. Chem. Commun. 1998, 1639.
15. Basavaiah, D.; Krishnamacharyulu, M.; Suguna Hyma, R.; Sarma, P. K. S.; Kumaragurubaran, N. J. Org. Chem. 1999, 64, 1197.
16. Basavaiah, D.; Sarma, P. K. S.; Bhavani, A. K. D. J. Chem. Soc., Chem. Commun. 1994, 1091.
17. Basavaiah, D.; Bhavani, A. K. D.; Sarma, P. K. S.; Pandiaraju, S. Synlett 1995, 243.
18. Basavaiah, D.; Pandiaraju, S. Tetrahedron 1996, 52, 2261.
19. Basavaiah, D.; Sarma, P. K. S. J. Chem. Soc., Chem. Commun. 1992, 955.
20. Basavaiah, D.; Krishnamacharyulu, M.; Suguna Hyma, R.; Pandiaraju, S. Tetrahedron Lett. 1997, 35, 2141.
21. 22,23
22. Manson, P. H.; Emslie, N. D. Tetrahedron 1994, 41, 12001.
23. Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr. 1989, 403.
24. 23
25. 13C NMR spectral data indicate the absence of any (Z)-isomer in the case of molecules 2a and 4a.
26. We have recently invoked the possibility of unusual 1,2-interactions in the Johnson-Claisen rearrangement to explain the stereoselectivity. See: Basavaiah, D.; Pandiaraju, S.; Krishnamacharyulu, M. Synlett 1996, 747.
27. Funabiki, T.; Hosomi, H.; Yoshida, S.; Tarama, K. J. Am. Chem. Soc. 1982, 104, 1560.