Synthesis of trisubstituted alkenes by reductive dehydroxylation of Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3

Tetrahedron Letters

Volumn 47, Issue 20, 2006, Pages 3475-3478

  Chandrasekhar, S ^a   Chandrashekar, G ^a   Vijeender, K ^a   Reddy, M Srinivasa ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Baylis Hillman adducts; Dehydroxylation; E and Z trisubstituted alkenes; PMHS B(C6F5)3

Indexed keywords

ALKENE DERIVATIVE; ALLYL ALCOHOL; ESTER DERIVATIVE; HYDROXYL GROUP; NITRILE; SILOXANE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CHEMICAL BOND; ELIMINATION REACTION; HYDROXYLATION; REDUCTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33646064428     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.014     Document Type: Article

References (38)

1. Baylis, A. B; Hillman, M. E. D. German Patent 2155-113, 1972; Chem. Abstr. 1972, 77, 34174q.
2. Basavaiah D., Rao P.D., and Hyma R.S. Tetrahedron 52 (1996) 8001-8062
3. Senokuchi K., Nakai H., Nakayama Y., Odagaki Y., Sakaki K., Kato M., Maruyama T., Miyazaki T., Ito H., Kamiyasu K., Kim S., Kawamaura M., and Hamanaka N. J. Med. Chem. 38 (1995) 2521-2523
4. Watanabe T., Hayashi K., Yoshimatsu S., Sakai K., Takeyama S., and Takashima K. J. Med. Chem. 23 (1980) 50-59
5. Anderson R.J., Coleman J.E., Piers E., and Wallace D.J. Tetrahedron Lett. 38 (1997) 317-320
6. Tanaka H., Kuroda A., Marusawa H., Hatanaka H., Kino T., Goto T., and Hashimoto M. J. Am. Chem. Soc. 109 (1987) 5031-5033
7. Ishibashi Y., Ohba S., Nishiyama S., and Yamamura S. Tetrahedron Lett. 37 (1996) 2997-3000
8. Marfat A., McGuirk P.R., and Helquist P. J. Org. Chem. 44 (1979) 3888-3901
9. Basavaiah D., Rao S.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891 and references cited therein
10. Das B., Banerjee J., and Ravindranath N. Tetrahedron 60 (2004) 8357-8361
11. Das B., Banerjee J., Ravindranath N., and Venkataiah B. Tetrahedron Lett. 45 (2004) 2425-2426
12. Das B., Majhi A., Banerjee J., Chowdhury N., and Venkateswarlu K. Tetrahedron Lett. 46 (2005) 7913-7915
13. Guriece A., and Goucaud A. New J. Chem. 15 (1991) 943
14. Rabe J., and Hoffmann H.M.R. Angew. Chem., Int. Ed. Engl. 22 (1983) 795
15. Hoffmann H.M.R., and Rabe J. J. Org. Chem. 50 (1985) 3849-3859
16. Das B., Banerjee J., Mahender G., and Majhi A. Org. Lett. 6 (2004) 3349-3352
17. Shadakshari U., and Nayak S.K. Tetrahedron Lett. 57 (2001) 4599-4602
18. Basavaiah D., Krishnamacharyulu M., Hyma R.S., Sarma P.K.S., and Kumaragurubaran N. J. Org. Chem. 64 (1999) 1197-1200
19. Das B., Banerjee J., Majhi A., and Mahender G. Tetrahedron Lett. 45 (2004) 9225-9227
20. Basavaiah D., and Sarma P.K.S. J. Chem. Soc., Chem. Commun. (1992) 955-995 and references cited therein
21. Pachamuthu K., and Vankar Y.D. Tetrahedron Lett. 39 (1998) 5439-5442
22. Chandrasekhar, S.; Babu B. N.; Chandrashekar, G. Review on tris(pentafluorophenyl)borane. Contribution for Electronic Encyclopedia of Organic Reagents for Organic Synthesis. eEROS, 2005 and references cited therein.
23. Our contributions with PMHS:. Chandrasekhar S., Chandrashekar G., Babu B.N., Vijeender K., and Venkatram Reddy K. Tetrahedron Lett. 45 (2004) 5497-5499
24. Chandrasekhar S., Babu B.N., Ahmed Md., Reddy M.V., Srihari P., Jagadeesh B., and Prabhakar A. Synlett (2004) 1303-1305
25. Chandrasekhar S., Reddy Ch.R., and Babu B.N. Tetrahedron Lett. 44 (2003) 2057-2059
26. Chandrasekhar S., Reddy Ch.R., and Rao R.J. Synlett (2001) 1561-1562
27. Chandrasekhar S., Reddy Ch.R., and Rao R.J. Tetrahedron 57 (2001) 3435-3438
28. Chandrasekhar S., Chandraiah L., and Reddy M.V. Synlett (2000) 1351-1353
29. Chandrasekhar S., Reddy Ch.R., and Ahmed Md. Synlett (2000) 1655-1657
30. Chandrasekhar S., Chandraiah L., Reddy Ch.R., and Reddy M.V. Chem. Lett. (2000) 780-781
31. Chandrasekhar S., and Ahmed Md. Tetrahedron Lett. 40 (1999) 9325-9327
32. Chandrasekhar S., Reddy M.V., and Chandraiah L. Synth. Commun. 29 (1999) 3981-3987
33. Chandrasekhar S., Reddy Y.R., and Reddy Ch.R. Chem. Lett. 29 (1998) 1273-1274
34. Chandrasekhar S., Reddy Y.R., and Ramarao C. Synth. Commun. 27 (1997) 2251-2254
35. Chandrasekhar S., Reddy C.R., and Babu B.N. J. Org. Chem. 67 (2002) 9080
36. +.
37. +.
38. +.