Simple metal alkoxides as effective catalysts for the hetero-aldol-Tishchenko reaction

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1427-1429

  Mascarenhas, Cheryl M ^a   Duffey, Matthew O ^a   Liu, Shih Yuan ^a   Morken, James P ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001926187     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990246c     Document Type: Article

References (19)

1. For a discussion on the reversibility of the aldol reaction, see: Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991; Vol. 2, pp 133-179.
2. (a) Kulpinski, M. S.; Nord, F. F. J. Org. Chem. 1943, 8, 256-270.
3. (b) Villiani, F. J.; Nord, F. F. J. Am. Chem. Soc. 1946, 68, 1674-1675.
4. (c) Villiani, F. J.; Nord, F. F. J. Am. Chem. Soc. 1947, 69, 2605-2608.
5. For representative examples of homo-aldol-Tishchenko reactions, see: (a) Casnati, G.; Pochini, A.; Salerno, G.; Ungaro, R. Tetrahedron Lett. 1974, 959-962.
6. (b) Fouquet, G.; Merger, F.; Platz, R. Liebigs Ann. Chem. 1979, 1591-1601.
7. (c) Villacorta, G.; San Filippo, J. J. Org. Chem. 1983, 48, 1151-1154.
8. (d) Okano, T.; Satou, Y.; Tamura, M.; Kiji, J. Bull. Chem. Soc. Jpn. 1997, 70, 1879-1885.
9. (e) Miyano, A.; Tashiro, D.; Kawasaki, Y.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 6901-6902.
10. For stoichiometric, stereoselective aldol-Tishchenko reactions, see: (a) Curran, D. P.; Wolin, R. L. Synlett 1991, 317-318.
11. (b) Baramee, A.; Chaichit, N.; Intawee, P.; Thebtaranonth, C.; Thebtaranonth, Y. J. Chem. Soc., Chem. Commun. 1991, 1016-1017.
12. (c) Bodnar, P. M.; Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 5674-5675.
13. (d) Abu-Hasanayn, F.; Streitwieser, A. J. Org. Chem. 1998, 63, 2954-2960.
14. Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089.
15. Lu, L.; Chang, H. Y.; Fang, J. M. J. Org. Chem. 1999, 64, 843-853.
16. 4 with BuMgCl to generate Ti(III) and, presumably, n-PrOMgCl, see: Herman, D. F.; Nelson, W. K. J. Am. Chem. Soc. 1953, 75, 3882-3887.
17. 4. This may be attributed to the presence of Ti(IV) alkoxides.
18. 4/BuLi as catalyst assumes that 0.2 equiv of benzaldehyde is converted to stilbene diol (which can be isolated from these experiments) in accord with a pinacol reaction mediated by titanium that has been reduced according to ref 7.
19. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.