Stabilization of ketone and aldehyde enols by formation of hydrogen bonds to phosphazene enolates and their aldol products

Journal of the American Chemical Society

Volumn 130, Issue 30, 2008, Pages 9668-9669

  Kolonko, Kristopher J ^a   Reich, Hans J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; DESILYLATION; DISSOCIATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STOICHIOMETRY;

ALCOHOLS; ALDEHYDES; ALKENES; HYDROGEN BONDING; KETONES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOPHOSPHORUS COMPOUNDS; SOLUTIONS; THERMODYNAMICS;

EID: 48249126202     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804221x     Document Type: Article

References (29)

1. Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, L.; Peters, E. M.; Peters, K.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1361-1363.
2. (a) Seebach, D.; Pietzonka, T. Chem. Ber. 1991, 124, 1837-1843.
3. Seebach, D.; Bezencon, O.; Jaun, B.; Pietzonka, T.; Matthews, J. L.; Kühnle, F. N.; Schweizer, W. B. Helv. Chim. Acta 1996, 79, 588-608.
4. (b) Solladié-Cavallo, A.; Crescenzi, B. Synlett 2000, 327-330.
5. Kobayashi, K.; Ueno, M.; Kondo, Y. Chem. Commun. 2006, 3128-3130.
6. (c) Ueno, M.; Hori, C.; Suzawa, K.; Ebisawa, M.; Kondo, Y. Eur. J. Org. Chem. 2005, 1965-1968.
7. Suzawa, K.; Ueno, M.; Wheatley, A. E.; Kondo, Y. Chem. Commun. 2006, 4850-4852.
8. (d) Imahori, T.; Kondo, Y. J. Am. Chem. Soc. 2003, 125, 8082-8083.
9. (e) Tanaka, Y.; Arakawa, M.; Yamaguchi, Y.; Hori, C.; Ueno, M.; Tanaka, T.; Imahori, T.; Kondo, Y. Chem. Asian J. 2006, 1, 581-585.
10. (a) Solladié-Cavallo, A.; Liptaj, T.; Schmitt, M.; Solgadi, A. Tetrahedron Lett. 2002, 43, 415-418.
11. (b) Fruchart, J.-S.; Lippens, G.; Kuhn, C.; Gras-Masse, H.; Melnyk, O. J. Org. Chem. 2002, 67, 526-532.
12. Fruchart, J.-S.; Gras-Masse, H.; Melnyk, O.; Fox, D. T.; Bergman, R. G. Tetrahedron Lett. 2003, 44, 2243.
13. 4).
14. The lithium enolate of dibenzyl ketone has been previously studied. (a) Gareyev, R.; Ciula, J. C.; Streitwieser, A. J. Org. Chem. 1996, 61, 4589-4593. Its behavior with P4 is nearly identical to that of 1a.
15. Hibbert, F.; Emsley, J. Adv. Phys. Org. Chem. 1990, 26, 255-379.
16. 7b have been previously reported. (a) Aladzheva, I. M.; Petrovskii, P. V.; Mastryukova, T. A.; Kabachnik, M. I. Zh. Obshch. Khim. 1980, 50, 1442-1445;
17. English translation, 1980, 50, 1161-1164.
18. Arnett, E. D.; Harrelson, J. A. Gazz. Chim. Ital. 1987, 117, 237-243.
19. (b) Bordwell, F. G.; McCallum, R. J.; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424-1427.
20. Shan, S.; Loh, S.; Herschlag, D. Science 1996, 272, 97-101.
21. Pan, Y.; McAllister, M. A. J. Org. Chem. 1997, 62, 8171-8176.
22. Jones, A. C.; Sanders, A. W.; Bevan, M. J.; Reich, H. J. J. Am. Chem. Soc. 2007, 29, 3492-3493.
23. Kumar, G. A.; McAllister, M. A. J. Org. Chem. 1998, 63, 6968-6972.
24. Wen, J. Q; Grutzner, J. B. J. Org. Chem. 1986, 51, 4220-4224.
25. 13C NMR spectroscopy.
26. 19F NMR spectroscopy. Saturation transfer measurements showed the enolate portion of 11 to be in exchange with the enolate 7 in solution.
27. For a previous RINMR study of a crossed aldol reaction see: Palmer, C. A.; Ogle, C. A.; Arnett, E. M. J. Am. Chem. Soc. 1992, 114, 5619-5625.
28. A similar adduct has been observed for the TAS enolate of cyclohexanone: Nakamura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, R. J. Org. Chem. 1983, 48, 932-945.
29. Cleland, W. W.; Frey, P. A.; Gerlt, J. A. J. Biol. Chem. 1998, 273, 25529-25532.