Axially chiral NHC-Pd(II) complexes in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant

Organic Letters

Volumn 9, Issue 5, 2007, Pages 865-868

  Chen, Tao ^a   Jiang, Jia Jun ^a   Xu, Qin ^a   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947147700     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063061w     Document Type: Article

References (41)

1. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph Series; American Chemical Society: Washington, DC, 1990.
2. Lloyd and Schwartz initiated the palladium-catalyzed aerobic oxidation of alcohols; see: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816-2819.
3. (b) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158.
4. For recent reviews, see: (a) Muzart, J. Tetrahedron 2003, 59, 5789-5816.
5. (b) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
6. (c) Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227-8241.
7. (d) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229.
8. (e) Rogers, M. M.; Stahl, S. S. In N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer: New York, 2007; Vol. 21, pp 21-
9. For some more selected examples, see: (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189.
10. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755.
11. (g) Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636-1639.
12. (h) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
13. (i) Schultz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035.
14. (j) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810-3813.
15. (k) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70, 3343-3352.
16. (a) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476.
17. (b) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202-8203.
18. (c) Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600-4603.
19. (d) Mueller, J. A.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 7005-7013.
20. (e) Mandal, S. K.; Sigman, M. S. J. Org. Chem. 2003, 68, 7535-7537.
21. (f) Mueller, J. A.; Goller, C. P.; Sigman, M. S. J. Am. Chem. Soc. 2004, 126, 9724-9734.
22. (g) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70, 3343-3352.
23. (h) Mueller, J. A.; Cowell, A.; Chandler, B. D.; Sigman, M. S. J. Am. Chem. Soc. 2005, 127, 14817-14824.
24. (i) Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63-65.
25. (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
26. (b) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835-837.
27. (c) Bagdanoff, J. T.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 353-357.
28. (d) Trend, R. M.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 4482-4483.
29. For reviews, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1209-1309.
30. (b) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619-636.
31. Selected examples, see: (a) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414.
32. (b) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173-3180.
33. (c) Xu, Q.; Duan, W. L.; Lei, Z. Y.; Zhu, Z. B.; Shi, M. Tetrahedron 2005, 61, 11225-11229.
34. (d) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101-4111.
35. Duan, W. L.; Shi, M.; Rong, G. B. Chem. Commun. 2003, 2916-2917.
36. The X-ray crystal data of racemic NHC-Pd(II) complex 1 has been deposited in CCDC with number 209242. For the details, see ref 7c. For a review of practical issues in kinetic resolutions, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26.
37. See the Supporting Information for details.
38. w, 0.543, 0.1246.
39. 2/(-)-sparteine (ref 5a), we initiated our investigation with the same model reaction and similar reaction conditions.
40. For detailed procedures of base and solvent screening trials, and the general procedure for the oxidative kinetic resolution of secondary alcohols, see the Supporting Information.
41. For the role of molecular sieves in Pd-catalyzed aerobic alcohol oxidation, see: Steinhoff, B. A.; King, A. E.; Stahl, S. S. J. Org. Chem. 2006, 71, 1861-1868.