Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones

Journal of the American Chemical Society

Volumn 129, Issue 43, 2007, Pages 12902-12903

  Sugawara, Yudai ^a   Yamada, Wataru ^a   Yoshida, Shunsuke ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBON DIOXIDE; KETONE; PROPARGYL ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALCOHOL METABOLISM; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MEYER SCHUSTER REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION; STOICHIOMETRY;

EID: 35948942005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074350y     Document Type: Article

References (21)

1. Meyer, K. H.; Schuster, K. Chem. Ber. 1922, 55, 819-823.
2. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed; John Wiley & Sons: New York, 2001; pp 423.
3. Vanadium: (a) Ernan, M. B.; Aul'chenko, I. S.; Kheifits, L. A.; Dulova, V. G.; Novikov, J. N.; Vol'pin, M. E. Tetrahedron Lett. 1976, 34, 2981-2984.
4. (b) Choudary, B. M.; Durga Prasad, A.; Valli, V. L. K. Tetrahedron Lett. 1990, 31, 7521-7522.
5. (c) Chabardes, P.; Kuntz, E.; Varagnat, J. Tetrahedron 1977, 33, 1775-1783.
6. Molybdenum: (d) Lorber, C. Y.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 853-856.
7. Titanium alkoxide: Chabardes, P. Tetrahedron Lett. 1988, 29, 6253-6256.
8. Under mild reaction conditions using a rhenium salt: Narasaka, K.; Kusama, H.; Hayashi, Y. Chem. Lett. 1991, 1413-1416.
9. (a) Fukuda, Y.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2013-2015.
10. (b) Georgy, M.; Boucard, V.; Campagne, J. J. Am. Chem. Soc. 2005, 127, 14180-14181.
11. (c) Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027-4029.
12. (d) Lopez, S. S.; Engel, D. A.; Dudley, G. B. Synlett 2007, 6, 949-953.
13. (e) Yu, M.; Li, G.; Wang, S.; Zhang, L. Adv. Synth. Catal. 2007, 349, 871-875.
14. (a) Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 1201-1202.
15. (b) Picquet, M.; Fernández, A.; Bruneau, C.; Dixneuf, P. H. Eur. J. Org. Chem. 2000, 2361-2366.
16. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531-7533.
17. (d) Cadierno, V.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 2716-2717.
18. (e) Cadierno, V.; Garcia-Garrido, S. E.; Gimeno, J. Adv. Synth. Catal. 2006, 348, 101-110.
19. Kayaki, Y.; Yamamoto, M.; Ikariya, T. J. Org. Chem. 2007, 72, 647-649 and references cited therein.
20. Yamada, W.; Sugawara, Y.; Cheng, H.-M.; Ikeno, T.; Yamada, T. Eur. J. Org. Chem. 2007, 2604-2607.
21. A high reaction temperature was required to complete the reaction of the secondary propargyl alcohol (see refs 3b, 3d, 5, 6a, 7c, and 7e).