Montmorillonite K10 clay catalyzed mild, clean, solvent free one-pot protection-isomerisation of the Baylis-Hillman adducts with alcohols

Chemistry Letters

Volumn , Issue 12, 2002, Pages 1212-1213

  Shanmugam, Ponnusamy ^a,b   Rajasingh, Paramasivan ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; LIGNAN; MONTMORILLONITE; NATURAL PRODUCT; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CLAY; ISOMERISM; PROTECTION; SYNTHESIS;

EID: 0037028362     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.1212     Document Type: Article

References (28)

1. a) M. Balogh and P. Laszlo, "Organic Chemistry Using Clays," Springer-Verlag, New York (1993).
2. b) G. W. Kabalka and R. M. Pagni, Tetrahedron, 53, 7999 (1997).
3. c) A. Corma, Chem. Rev., 95, 559 (1995).
4. a) S. E. Derewes and G. H. P. Roos, Tetrahedron, 44, 4653 (1988).
5. b) E. Cignek, in "Organic Reactions," ed. by L. A. Paquette, Wiley & Sons, New York (1997), Vol. 51, pp 201-350.
6. c) H. M. R. Hofmann, U. Eggert, and W. Poly, Angew. Chem., Int. Ed. Engl., 26, 1015 (1987).
7. d) D. Basavaiah, K. Muthukumaran, and B. Sreenivasulu, Synthesis, 2000, 545.
8. e) D. Basavaiah, K. Padmaja, and T. Satyanarayana, Synthesis, 2000, 1662, and references cited therein.
9. f) H. S. Kim, T. Y. Kim, K. Y. Ley, Y. M. Chung, H. J. Lee, and J. N. Kim, Tetrahedron Lett., 41, 2613 (2000).
10. g) A. Foucaud and F. E. Guemmount, Bull. Soc. Chim. Fr., 1989, 403.
11. h) D. Basavaiah, M. Krishnamacharyulu, R. S. Hyma., P. K. S. Sarma, and N. Kumaragurubaran, J. Org. Chem., 64, 1197 (1999).
12. i) J. N. Kim and K. Y. Lee, Curr. Org. Chem., 6, 627 (2002).
13. a) P. Shanmugam and V. Nair, Synth. Commun., 26, 3007 (1996).
14. b) P. Shanmugam, Synth. Commun., 29, 4409 (1999).
15. c) P. Shanmugam and R. L. Varma, Indian J. Chem., Sect. B, 40B, 1258 (2001).
16. d) P. Shanmugam and P. R. Singh, Synlett, 2001, 1314.
17. N. G. Lewis and L. B. Davin, in "Comprehensive Natural Products Chemistry," ed. by D. Barton, K. Nakanishi, and O. Meth-Cohn, Pergamon Press, Oxford (1999), Vol. 1, pp 639-712.
18. P. Shanmugam and P. Rajasingh, under preparation.
19. B. Giese, "Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds," Pergamon Press, Oxford (1986).
20. J. Fossey, D. Lefort, and J. Sorba, "Free Radicals in Organic Chemistry," Wiley & Sons, Chichester (1995).
21. C. P. Jasperse, D. P. Curran, and T. L. Fevig, Chem. Rev., 91, 1237 (1991).
22. S. Janardhanam, P. Shanmugam, and K. Rajagopalan, J. Org. Chem., 58, 7782 (1993).
23. P. Shanmugam, R. Srinivasan, and K. Rajagopalan, Tetrahedron, 53, 6085 (1997).
24. P. Shanmugam, R. Srinivasan, and K. Rajagopalan, Tetrahedron, 53, 11685 (1997).
25. D. Basavaiah, N. Kumaragurubaran, D. S. Sharada, and R. M. Reddy, Tetrahedron, 57, 8167 (2001).
26. 1H NMR spectra of the isomerised product 3 showed a peak at δ 7.92 for the presence of E-vinylic proton.
27. 1H NMR.
28. 3: C, 73.03. H, 6.13% Found: C, 73.00, H. 6.08%.