One-pot oxidative allylation of Morita-Baylis-Hillman adducts with allyltrimethylsilane promoted by Dess-Martin periodinane/boron trifluoride-diethyl ether complex

Synthesis

Volumn , Issue 3, 2008, Pages 0469-0473

  Yadav, Jhillu S ^a   Reddy, B V Subba ^a   Singh, Ashutosh Pratap ^a   Basak, Ashok K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

keto esters; Allylations; Conjugate additions; Hypervalent iodine reagents; Morita Baylis Hillman adducts

Indexed keywords

DERIVATIVES; ETHERS; OXIDATION; REACTION KINETICS;

HYPERVALENT IODINE REAGENTS; MORITA-BAYLIS-HILLMAN ADDUCTS; OXIDATIVE ALLYLATION;

BORON COMPOUNDS;

ALLYLTRIMETHYLSILANE; BORON TRIFLUORIDE; ESTER DERIVATIVE; ETHER;

ALLYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; DESS MARTIN OXIDATION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS;

EID: 39349091262     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032020     Document Type: Article

References (30)

1. Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
2. (a) Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
3. (b) Basavaiah, D.; Dharma Rao, P.; Suguna, H. R. Tetrahedron 1996, 52, 8001.
4. (c) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
5. (a) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6737.
6. (b) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385.
7. (c) Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675.
8. (d) Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821.
9. (e) Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341.
10. (a) Drewes, S. E.; Emslie, N. D. J. Chem. Soc., Perkin Trans. 1 1982, 2079.
11. (b) Hoffmann, H. M. R.; Rabe, J. Helv. Chim. Acta 1984, 67, 413.
12. (c) Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50, 3849.
13. (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed. Engl. 1985, 24, 94.
14. (b) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
15. (c) Ameer, F.; Drewes, S. E.; Hoole, R. F. A.; Kaye, P. T.; Pitchford, A. T. J. Chem. Soc., Perkin Trans. 1 1985, 2713.
16. (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
17. (b) Marshall, J. A. Chemtracts 1992, 5, 75.
18. (c) Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23.
19. (d) Colvin, E. In Silicon in Organic Synthesis; Butterworth: London, 1981, 97.
20. (e) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
21. Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
22. (a) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic: San Diego, 1997, 256.
23. (b) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271.
24. (c) Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812.
25. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
26. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
27. (a) Nicolaou, K. C.; Baran, P. S.; Zong, Y.-L.; Sugita, K. J. Am. Chem. Soc. 2002, 124, 2212.
28. (b) Nicolaou, K. C.; Mathison, C. J. N. Angew. Chem. Int. Ed. 2005, 44, 5992.
29. (c) Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, (ix), 26.
30. (d) Lawrence, N. J.; Crump, J. P.; McGown, A. T.; Hadfield, J. A. Tetrahedron Lett. 2001, 42, 3939.