Ireland-Claisen rearrangement of secondary allyl acetate revisited: Inevitable C-silylation circumvented by one-pot application of excessive LDA/TMSCl and TBAF

Tetrahedron Letters

Volumn 53, Issue 17, 2012, Pages 2177-2180

  Liu, Di ^a   Yu, Xiaoming ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Allyl acetate; C silylation; High yield; Ireland Claisen rearrangement; One pot protocol

Indexed keywords

ALLYL ACETATE; ALLYL COMPOUND; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CLAISEN REARRANGEMENT; ONE POT SYNTHESIS; SILYLATION; STOICHIOMETRY;

EID: 84863369465     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.071     Document Type: Article

References (27)

1. R.E. Ireland, and R.H. Mueller J. Am. Chem. Soc. 94 1972 5897 5898
2. A.M.M. Castro Chem. Rev. 104 2004 2939 3002
3. C.M. McFarland, and M.C. McIntosh M. Hiersemann, U. Nubbemeyer, The Claisen Rearrangement 2007 Wiley-VCH Weinheim 117
4. C.M. Beaudry, and D. Trauner Org. Lett. 7 2005 4475 4477
5. Y. Zhou, and J.G. Millar Synlett 2010 2319 2321
6. F. He, Y. Bo, J.D. Altom, and E.J. Corey J. Am. Chem. Soc. 121 1999 6771 6772
7. J.C. McKew, and M.J. Kurth J. Org. Chem. 58 1993 4589 4595
8. E. Brenna, C. Fuganti, P. Grasselli, and S. Serra Eur. J. Org. Chem. 2001 1349 1357
9. M.G. Banwell, and D.W. Lupton Org. Biomol. Chem. 3 2005 213 215
10. G.E. Keck, and R.R. Webb J. Am. Chem. Soc. 103 1981 3173 3177
11. G. Liu, and S.S. Stahl J. Am. Chem. Soc. 129 2007 6328 6335
12. G. Pattenden, and G.F. Smith Tetrahedron Lett. 31 1990 6557 6560
13. E.-M. Moffatt, and E.J. Thomas Tetrahedron 55 1999 3723 3734
14. G.E. Keck, and R.R. Webb J. Org. Chem. 47 1982 1302 1309
15. D.A. Clark, A.A. Kulkarni, K. Kalbarczyk, B. Schertzer, and S.T. Diver J. Am. Chem. Soc. 128 2006 15632 15636
16. L.F. Tietze, C. Stadler, N. Böhnke, G. Brasche, and A. Grube Synlett 2007 485 487
17. N. Yoshikawa, L. Tan, N. Yasuda, R.P. Volante, and R.D. Tillyer Tetrahedron Lett. 45 2004 7261 7264
18. S. Ceccarelli, U. Piarulli, and C. Gennari Tetrahedron Lett. 40 1999 153 156
19. S. Pichlmair, M. Ruiz, K. Basu, and L.A. Paquette Tetrahedron 62 2006 5178 5194
20. T.R. Hoye, P.E. Humpal, and B. Moon J. Am. Chem. Soc. 122 2000 4982 4983
21. T. Frank, and H. Guenter J. Fluorine Chem. 125 2004 1593 1608
22. M. Rowley, M. Tsukamoto, and Y. Kishi J. Am. Chem. Soc. 111 1989 2735 2737
23. T. Okabayashi, A. Iida, K. Takai, Y. Nawate, T. Misaki, and Y. Tanabe J. Org. Chem. 72 2007 8142 8145
24. V. Enev, D. Stojanova, and S. Bienz Helv. Chim. Acta 79 1996 391 404
25. M.R. Nahm, L. Xin, J.R. Potnick, C.M. Yates, P.S. White, and J.S. Johnson Angew. Chem., Int. Ed. 44 2005 2377 2379
26. B.M. Trost, J.P.N. Papillon, and T. Nussbaumer J. Am. Chem. Soc. 127 2005 17921 17937
27. M. Iguchi, H. Doi, S. Hata, and K. Tomioka Chem. Pharm. Bull. 52 2004 125 129