Palladium catalysts for aerobic oxidative kinetic resolution of secondary alcohols based on mechanistic insight

Organic Letters

Volumn 5, Issue 1, 2003, Pages 63-65

  Jensen, David R ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBENOID; LIGAND; PALLADIUM; SPARTEINE; OXYGEN; PALLADIUM CHLORIDE;

ARTICLE; CATALYST; CHIRALITY; COMPLEX FORMATION; KINETICS; OXIDATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALCOHOLS; CATALYSIS; KINETICS; MOLECULAR STRUCTURE; OXYGEN; PALLADIUM;

EID: 0037986275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027190y     Document Type: Article

References (28)

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2. Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475.
3. Simultaneously and independently, a closely related aerobic oxidative kinetic resolution of secondary alcohols was reported; see: Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
4. Mueller, J A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202.
5. rel = 1n[(1 - C)(1 - ee)]/ln[(1 - C)(1 + ee)], where C = conversion and ee = enantiomeric excess. See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
6. 3, xantphos, and BINAP.
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9. After our paper was submitted, the preparation of Pd(allyl)Cl-carbene complexes was independently reported; see: Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053.
10. Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock, P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J. Organomet. Chem. 2001, 617-618, 635.
11. For the use of chromatography to purify Pd(II)-carbene complexes, see: Weskamp, T.; Bohm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348.
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13. Protonolysis proceeds smoothly for N-aryl carbene complexes; however, protonolysis of N-alkyl carbene complexes leads to a mixture of products.
14. 2-carbene dimers are inert towards alcohol oxidation without added base.
15. NMR experiments indicate that (-)-sparteine does not substitute for the carbene ligand.
16. (-)-Sparteine could act as a transient ligand, a base, or both.
17. Asymmetric catalysis has been accomplished with a racemic catalyst and an enantiopure activator; for an example, see: Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532.
18. Achiral and meso additives have been used with an enantiopure ligand; for an example, see: Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929.
19. For the use of achiral ligands with chiral conformations, see: (a) Hashihayata, T.; Ito, Y.; Katsuki, T. Synlett 1996, 1079-1081. (b) Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron 1997, 53, 9541-9552. (c) Miura, K.; Katsuki, T. Synlett 1999, 783-785. (d) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802-1803.
20. For the use of achiral ligands with chiral conformations, see: (a) Hashihayata, T.; Ito, Y.; Katsuki, T. Synlett 1996, 1079-1081. (b) Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron 1997, 53, 9541-9552. (c) Miura, K.; Katsuki, T. Synlett 1999, 783-785. (d) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802-1803.
21. For the use of achiral ligands with chiral conformations, see: (a) Hashihayata, T.; Ito, Y.; Katsuki, T. Synlett 1996, 1079-1081. (b) Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron 1997, 53, 9541-9552. (c) Miura, K.; Katsuki, T. Synlett 1999, 783-785. (d) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802-1803.
22. For the use of achiral ligands with chiral conformations, see: (a) Hashihayata, T.; Ito, Y.; Katsuki, T. Synlett 1996, 1079-1081. (b) Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron 1997, 53, 9541-9552. (c) Miura, K.; Katsuki, T. Synlett 1999, 783-785. (d) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802-1803.
23. For the use of achiral ligands with chiral conformations, see: (a) Hashihayata, T.; Ito, Y.; Katsuki, T. Synlett 1996, 1079-1081. (b) Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron 1997, 53, 9541-9552. (c) Miura, K.; Katsuki, T. Synlett 1999, 783-785. (d) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802-1803.
24. For a review of achiral additives in asymmetric catalysis, see: (a) Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570. (b) For a specific example where a reversal in enantiofacial selectivity was observed by addition of an achiral additive, see: Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
25. For a review of achiral additives in asymmetric catalysis, see: (a) Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570. (b) For a specific example where a reversal in enantiofacial selectivity was observed by addition of an achiral additive, see: Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
26. For the use of similar chiral carbene ligands, see: Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225.
27. For examples of the use of 1:1 Pd-carbene complexes in catalysis, see: (a) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69. (b) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
28. For examples of the use of 1:1 Pd-carbene complexes in catalysis, see: (a) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69. (b) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.