Palladium-catalyzed enantioselective oxidation of alcohols: A dramatic rate acceleration by Cs2CO3/t-BuOH

Organic Letters

Volumn 5, Issue 6, 2003, Pages 835-837

  Bagdanoff, Jeffrey T ^a   Ferreira, Eric M ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBONIC ACID DERIVATIVE; CESIUM; HYDROXIDE; PALLADIUM; ALCOHOL DERIVATIVE; TERT BUTYL ALCOHOL;

ACCELERATION; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; KINETICS; OXIDATION; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALCOHOLS; CARBONATES; CATALYSIS; CESIUM; KINETICS; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM; TERT-BUTYL ALCOHOL;

EID: 0038276940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027463p     Document Type: Article

References (14)

1. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
2. Simultaneous to our publication a related system was reported; see: Jensen., D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475.
3. 2; see: Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
4. Recently, Stahl has been studying the mechanistic details of related, non-asymmetric systems; see: (a) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179. (b) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766. (c) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
5. Recently, Stahl has been studying the mechanistic details of related, non-asymmetric systems; see: (a) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179. (b) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766. (c) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
6. Recently, Stahl has been studying the mechanistic details of related, non-asymmetric systems; see: (a) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179. (b) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766. (c) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
7. For discussions on kinetic resolution, see: (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. (b) Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. (c) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Ed.; Wiley & Sons: New York, 1988; Vol. 18, pp 249-330.
8. For discussions on kinetic resolution, see: (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. (b) Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. (c) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Ed.; Wiley & Sons: New York, 1988; Vol. 18, pp 249-330.
9. For discussions on kinetic resolution, see: (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. (b) Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. (c) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Ed.; Wiley & Sons: New York, 1988; Vol. 18, pp 249-330.
10. Bagdanoff, J. T.; Ferreira, E. M.; Trend, R. M.; Stoltz, B. M. Unpublished results.
11. 2 and has recently published a kinetic study of the effect; see: Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202.
12. 5c
13. Although we have never experienced an accident, all reactions must be performed with appropriate caution in a fume hood due to the flammable nature of mixtures of oxygen and organic solvents.
14. 2 were less effective in terms of both enantioselectivity and reactivity.