The zirconium alkoxide-catalyzed aldol-tishchenko reaction of ketone aldols

Chemistry - A European Journal

Volumn 11, Issue 10, 2005, Pages 3010-3021

  Schneider, Christoph ^a   Hansch, Markus ^a   Weide, Timo ^a,b  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alcohols; Aldol reaction; Diastereoselectivity; Tishchenko reduction; Zirconium

Indexed keywords

ACIDITY; ALCOHOLS; CATALYSIS; CHEMICAL MODIFICATION; ESTERS; METHANE; REDUCTION; SOLVENTS; SUBSTITUTION REACTIONS; THERMODYNAMICS; ZIRCONIUM;

ALDOL REACTION; DISTEREOSELECTIVITY; MONOESTERS; TISHCHENKO REDUCTION;

KETONES;

EID: 18744399050     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400951     Document Type: Article

References (32)

1. a) M. S. Kulpinski, F. F. Nord, J. Org. Chem. 1943, 8, 256;
2. b) F. J. Villani, F. F. Nord, J. Am. Chem. Soc. 1947, 69, 2605.
3. For an excellent review see: R. Mahrwald, Curr. Org. Chem. 2003, 7, 713.
4. F. Abu-Hasanayn, A. Streitwieser, J. Org. Chem. 1998, 63, 2954.
5. L. F. Tietze, Chem. Rev. 1996, 96, 115.
6. a) A. Baramee, N. Chaichit, P. Intawee, C. Thebtharononth, Y. Thebtharononth, J. Chem. Soc. Chem. Commun. 1991, 1016;
7. b) P. M. Bodnar, J. T. Shaw, K. A. Woerpel, J. Org. Chem. 1997, 62, 5674.
8. R. Mahrwald, B. Costisella, Synthesis 1996, 1087.
9. C. Delas, C. Moise, Synthesis 2000, 251.
10. Y. Horiuchi, M. Taniguchi, K. Oshima, K. Utimoto, Tetrahedron Lett. 1995, 36, 5353.
11. a) D. P. Curran, R. L. Wolin, Synlett 1991, 317;
12. b) L. Lu, H.-Y. Chang, J. Org. Chem. 1999, 64, 843.
13. C. M. Mascarenhas, M. O. Duffey, S.-Y. Liu, J. P. Morken, Org. Lett. 1999, 1, 1427.
14. C. M. Mascarenhas, S. P. Miller, P. S. White, J. P. Morken, Angew. Chem. 2001, 113, 621;
15. Angew. Chem. Int. Ed. 2001, 40, 601.
16. V. Gnanadesikan, Y. Horiuchi, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7782.
17. J. Mlynarski, M. Mitura, Tetrahedron Lett. 2004, 45, 7549.
18. I. Simpura, V. Nevalainen, Tetrahedron Lett. 2001, 42, 3905;
19. I. Simpura, V. Nevalainen, Tetrahedron 2003, 59, 7535.
20. C. Schneider, M. Hansch, Chem. Commun. 2001, 1218.
21. C. Schneider, M. Hansch, Synlett 2003, 837.
22. For an excellent review, see S. Yamasaki, M. Kanai, M. Shibasaki, Chem. Eur. J. 2001, 7, 4067.
23. D. C. Bradley, R. C. Mehrotra, W. Wardlaw, J. Chem. Soc. 1952, 2027.
24. D. C. Bradley, R. C. Mehrotra, W. Wardlaw, J. Chem. Soc. 1952, 4204.
25. See, for example: B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003;
26. N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466.
27. T. Imamoto, Y. Tetsuo, M. Yokoyama, Tetrahedron Lett. 1983, 24, 5233.
28. R. K. Haynes, Aust. J. Chem. 1978, 31, 1737.
29. G. Wittig, M. Leo, Ber. Dtsch. Chem. Ges. B 1931, 64, 2395.
30. D. A. Evans, A. H. Hoveyda, J. Am. Chem. Soc. 1990, 112, 6447.
31. S. D. Rychnovsky, B. N. Rogers, T. I. Richardson, Acc. Chem. Res. 1998, 31, 9.
32. R. W. Hoffmann, M. Bewersdorf, M. Krüger, W. Mikolaiski, R. Stürmer, Chem. Ber. 1991, 124, 1243.