Discovery of a practical direct O2-coupled wacker oxidation with Pd[(-)-sparteine]Cl2

Organic Letters

Volumn 8, Issue 18, 2006, Pages 4117-4120

  Cornell, Candace N ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLORO(SPARTEINE)PALLADIUM(II); DRUG DERIVATIVE; ORGANOMETALLIC COMPOUND; OXYGEN; PALLADIUM; SPARTEINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; SPARTEINE;

EID: 33748945849     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061662h     Document Type: Article

References (23)

1. (a) Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, A. Angew. Chem. 1962, 74, 93-102.
2. For reviews on Wacker oxidations see: (b) Takacs, J. M.; Jiang, X.-t. Curr. Org. Chem. 2003, 7, 369-396.
3. (c) Tsuji, J. Synthesis 1984, 369-384.
4. For recent book chapters on Wacker oxidations see: (a) Monflier, E.; Mortreux, A. In Aqueous-Phase Organometallic Catalysis, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VHC: Weinheim, Germany, 2004; pp 481-487.
5. (b) Hintermann, L. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VHC: Weinheim, Germany, 2004; Vol. 2, pp 379-388.
6. (c) Jira, R. In Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Hermann, W. A., Eds.; Wiley-VHC: Weinheim, Germany. 2002; Vol. 1, pp 386-405.
7. Crimmins, M. T.; Brown, B. H. J. Am. Chem. Soc. 2004, 126, 10264-10266.
8. Schmidt, D. R.; Park, P. K.; Leighton, J. L. Org. Lett. 2003, 5, 3535-3537.
9. For the total synthesis of Dolabelide D. see: Park, P. K.; O'Malley, S. J.; Schmidt, D. R.; Leighton, J. L. J. Am. Chem. Soc. 2006, 128, 2796-2797.
10. Cornell, C. N.; Sigman, M. S. J. Am. Chem. Soc. 2005, 127, 2796-2797.
11. (a) Clement, W. H.; Selwitz, C. M. J. Org. Chem. 1964, 29, 241-243.
12. (b) Tang, H. G.; Sherrington, D. C. J. Mol. Catal. 1994, 94, 7-17.
13. (c) Smith, A. B., III; Cho, Y. S.; Friestad, G. K. Tetrahedron Lett. 1998, 39, 8765-8768.
14. For reviews on Pd-catalyzed aerobic alcohol oxidations see: (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229.
15. (b) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
16. (c) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
17. (d) Muzart, J. Tetrahedron 2003, 59, 5789-5816.
18. Mueller, J. A.; Cowell, A.; Chandler, B. D.; Sigman, M. S. J. Am. Chem. Soc. 2005, 127, 14817-14824.
19. Gligorich, K. M.; Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 2794-2795.
20. Balija, A. M.; Stowers, K. J.; Schultz, M. J.; Sigman, M. S. Org. Lett. 2006, 8, 1121-1124.
21. Mitsudome, T.; Umetani, T.; Nosaka, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Angew. Chem., Int. Ed. 2006, 45, 481-485.
22. Kang, S.-K.; Jung, K.-Y.; Chung, J.-U.; Namkoong, E.-Y.; Kim, T.-H. J. Org. Chem. 1995, 60, 4678-4679.
23. Enantiomercially enriched 1-hydroxy-1-phenyl-3-butanone was synthesized by using the method reported in: Lee, J.-Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837-1839.