Mechanistic and synthetic aspects of the benzilic acid and ester rearrangements

Mini-Reviews in Organic Chemistry

Volumn 4, Issue 4, 2007, Pages 310-316

  Burke, Anthony J ^a   Marques, C S ^a  

^a UNIVERSITY OF ÉVORA   (Portugal)

Author keywords

Benzilic acid rearrangement; Benzilic ester rearrangement; Retro benzilic acid rearrangement; Synthesis; 1,2 rearrangement

Indexed keywords

ESTERS; MOLECULES;

BENZILIC ACID; BENZILIC ACID REARRANGEMENT; BENZILIC ESTER; BENZILIC ESTER REARRANGEMENT; MECHANISTIC STUDIES; MECHANISTICS; RETRO-BENZILIC ACID REARRANGEMENT; TARGET MOLECULE; [1,2] REARRANGEMENT;

SYNTHESIS (CHEMICAL);

EID: 36749048848     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019307782411707     Document Type: Review

References (34)

1. (a) Liebig, J. Justus Liebigs Ann. Chem., 1838, 25, 27.
2. (b) March, J. Advanced Organic Chemistry, 4th ed., Wiley-Interscience, New York, 1992.
3. Selman, I.R.; Eastham, J.F. Quat. Rev., 1960, 14, 221.
4. Gill, G.B. In Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I. Ed.; Pergamon Press, New York, 1991; Vol. 3, pp. 821.
5. Bowden, K.; Williams, K.D. J. Chem. Soc. Perkin Trans. 2, 1994, 77.
6. Collins, C.J.; Neville, O.K. J. Am. Chem. Soc., 1951, 73, 2471.
7. Marques, C.S.; Moura, N. Burke, A.J. Tetrahedron Lett., 2006, 47, 6049.
8. Marques, C.S.; Moura, M.M.; Burke, A.J; Furtado, R.F. Tetrahedron Lett., in press.
9. Yamabe, S.; Tsuchida, N.; Yamazaki, S. J. Org. Chem., 2006, 71, 1777.
10. Screttas, C.G.; Micha-Screttas, M.; Cazianis, C.T. Tetrahedron Lett., 1993, 24, 3287.
11. Rajyagura, I.; Rzepa, H.S. J. Chem. Soc. Perkin Trans. II, 1987, 1819.
12. (a) Comisar, C.; Savage, P.E. Green Chem., 2005, 7, 800.
13. (b) Comisar, C.; Savage, P.E. Ind. Eng. Chem. Res., 2007, 46, 1690.
14. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon, Oxford, 1983.
15. Brady, BA.; Geoghegan, M.; O'Sullivan, W.I. Proc. R. Ir. Acad., 1989, 89B, 105.
16. Burke, A.J.; Schmalle, H.W.; Brady, B.A.; O'Sullivan, W.I. Acta Cryst., 2000, C56, 484.
17. Deb, S.; Chakraborti, R.; Ghatak, U.R. Synth. Commun., 1993, 23, 913.
18. Rubin, M.B. Chem Rev., 1975, 75, 177.
19. Askin, D.; Reamer, R.A.; Jones, T.K.; Volante, R.P.; Shinkai, I. Tetrahedron Lett., 1989, 30, 671.
20. Askin, D.; Reamer, R.A.; Joe, D.; Volante, R.P.; Shinkai, I. Tetrahedron Lett., 1989, 30, 6121.
21. (a) Baumann, K.; Bacher, M.; Steck, A.; Wagner, T. Tetrahedron, 2004, 60, 5965.
22. (b) Baumann, K.; Bacher, M.; Damont, A.; Högenauer, K.; Steck, A. Tetrahedron, 2003, 59, 10075.
23. (c) Baumann, K.; Bacher, M.; Damont, A.; Steck, A. Tetrahedron Lett., 2004, 45, 549,
24. Fisher, M.J.; Chow, K.; Villalobos, A.; Danishefsky, S.J. J. Org. Chem., 1991, 56, 2900.
25. Luengo, J.I.; Konialian, A.L.; Holt, D.A. Tetrahedron Lett., 1993, 34, 991.
26. Koch, G.; Jeck, R.; Hartmann, O.; Küsters, E. Org. Process Res. Dev., 2001, 5, 211.
27. Nicolaou, K.C.; Chakraborthy, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 2471.
28. Stoltz, B.M.; Wood, J.L. Tetrahedron Lett., 1996, 37, 3929.
29. Black, D. St. C. J. Chem. Soc. Chem. Commun., 1967, 311;
30. Black, D. St. C.; Srivastava, R.C. J. Aust. J. Chem. 1969, 22, 1439.
31. Abrahams, B.F.; Hudson, T.A.; Robson, R. Chem. Eur. J., 2006, 12, 7095.
32. Hotchkiss, D.J.; Jenkinson, S.F.; Storer, Heinz, T.; Fleet G.W.J. Tetrahedron Lett., 2006, 47, 315.
33. Prof. George Fleet, Department of Clemistry, University of Oxford, personal communication.
34. Hatsui, T.; Wang, J.-J.; Ikeda, S.-Y.; Takeshita, H. Synlett, 1995, 35.