Palladium catalysed conversion of vinyl bromo allylic alcohols into vinylic carbonyl compounds and oxidation of secondary alcohols to ketones

Tetrahedron

Volumn 52, Issue 37, 1996, Pages 12291-12298

  Pitre, Sangceta V ^a   Vankar, Padma S ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030576875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00715-6     Document Type: Article

References (28)

1. 1. Part 4 "General Synthetic Methods". For part 3 see Ram Reddy, M. V.; Kumareswaran, R. and Vankar, Y. D. Tetrahedron Lett. 1995, 36, 6751.
2. 2. Part of this work was presented in 'ICOS-10, IUPAC at Bangalore, December 11-16, 1994'.
3. 3. (i) Heck, R. F. 'Palladium Reagents in Organic Synthesis', Academic Press, London, 1985.
4. (ii) Heck, R.F. 'Organic Reactions' 1982, 27, 345.
5. (iii) Heck, R.F. 'Comprehensive Organic Synthesis' Trost, B. M. Ed.; Pergamon Press, Oxford, 1991, Vol. 4, p. 833.
6. (iv) Jeffery, T. J. Chem Soc.,Chem. Commun. 1991, 324.
7. (v) Idem, Tetrahedron Lett. 1991, 32, 2121.
8. 4. Reissig, H.-U. 'Organic Synthesis Highlights' Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K. and Reissig, H.-U. Ed.; VCH, Weinheim, 1991, p. 174.
9. 5. (i) Laschat, S.; Narjes, F. and Overman, L. E. Tetrahedron 1994, 50, 347 and references cited therein.
10. (ii) Nylund, C. S.; Klopp, J. M. and Weinreb, S. M. Tetrahedron Lett. 1994, 35, 4287.
11. 6. Nagashima, H., Sato, K. and Tsuji, J. Chemistry Lett. 1981, 1605.
12. 7. Tsuji, J.; Nagashima, H. and Sato, K. Tetrahedron Lett. 1982, 23, 3085.
13. 8. Compound 2f was synthesised through a sequence of reactions as shown below: (equation presented)
14. 9. Tamaru, Y.; Yamamoto, Y.; Yamada, Y. and Yoshida, Z.-I. Tetrahedron Lett. 1979, 20, 1401.
15. 10. (i) For a comprehensive review please see Johnstone, R. A. W.; Wilby, A. H. and Entwistle, I. D. Chem. Rev. 1985, 85, 129.
16. (ii) Bandodakar, B. S. and Nagendrappa, G. J. Organomet. Chem. 1992, 430, 373 and references cited therein,
17. (iii) Wang, G.-Z. and Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1992, 980 and references cited therein,
18. (iv) Iyer, S. and Varghese, J. P. J. Chem. Soc., Chem.Commun. 1995, 465.
19. 11. Sokolov, N. A.; Chernov, Yu. G. and Glazkov, Yu. V. Collec. Czech. Chem. Commun. 1961, 305.
20. 12. Denmark, S. E.; Habermas, K. L. and Hite, G. A. Helv. Chim. Acta 1988, 71, 168.
21. 13. Akano M.; Hori, I. and Midorikawa, H. Sci. Pap. Inst. Phys. Chem. Res. 1968, 62, 127.
22. 14. (i) Coates, R. M.; Senter, P. D. and Baker, W. R. J. Org. Chem. 1982, 47, 3597.
23. (ii) Rajamannar, T. and Balasubramanian, K. K. Tetrahedron Lett. 1988, 29, 5789.
24. 15. House, H. O.; Huber, L. E. and Umen, M. J. J. Am. Chem. Soc. 1972, 94, 8471.
25. 16. Rousseau, G.; LePerchec, P. and Conia, J. M. Synthesis 1978, 67.
26. 17. Carlsson, S. and Lawesson, S.-O. Tetrahedron 1982, 38, 413.
27. 18. Zhang, P. and Li, L.-c. Synth. Commun. 1986, 16, 957.
28. 2: C, 46.37; H, 5.62. Found: C, 46.81; H, 5.03 %.