Highly efficient catalytic asymmetric epoxidation of allylic alcohols by an oxovanadium-substituted polyoxometalate with a regenerative TADDOL-derived hydroperoxide

Organic Letters

Volumn 5, Issue 5, 2003, Pages 725-728

  Adam, Waldemar ^a   Alsters, Paul L ^b   Neumann, Ronny ^c   Saha Möller, Chantu R ^a   Seebach, Dieter ^d   Zhang, Rui ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

^c WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^d ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; HYDROPEROXIDE DERIVATIVE; OXYGEN; VANADIUM DERIVATIVE;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DERIVATIZATION; ENANTIOMER; ENANTIOSELECTIVITY; ENERGY ABSORPTION; EPOXIDATION; QUANTUM YIELD; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0038133366     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027498p     Document Type: Article

References (38)

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7. For reviews, see: (a) Mizuno, N.; Misono, M. Chem. Rev. 1998, 98, 199-218. (b) Hill, C. L.; Prosser-McCartha, C. M. Coord. Chem. Rev. 1995, 143, 407-455. (c) Kozhevinikov, I. V. Chem. Rev. 1998, 98, 171-198. (d) Neumann, R. Prog. Inorg. Chem. 1998, 47, 317-370. (e) Finke, R. G. In Polyoxometalate Chemistry; Pope, M. T., Müller, A., Eds; Kluwer Academic Publisher: Dordrecht, The Netherlands, 2001; pp 363-390.
8. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
9. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
10. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
11. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
12. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
13. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
14. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
15. For leading examples in catalysis, see: (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-538. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P. ; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074. (d) Bösing, M.; Nöh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259. (e) Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. J. Am. Chem. Soc. 1998, 120, 9267-9272. (f) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831-9842. (g) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 12, 2011-2014. (h) Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. In press.
16. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; pp 48-62.
17. For example, even in the presence of molecular sieves, the Sharpless-Katsuki epoxidation still requires 5-10 tool % of Ti catalyst to protect the latter from adventitious water; see: Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley: New York, 2000; pp 231-280.
18. Hydroperoxides such as tert-butyl hydroperoxide are known to serve as the oxygen source for POM-catalyzed oxidations; however, these epoxidations are of limited success in view of the low reactivity and, in most cases, undesirable radical-type reactions, see: (a) Faraj, M.; Hill, C. L. J. Chem. Soc., Chem. Commun. 1987, 1487-1489. (b) Neumann, R.; Khenkin, A. M. Inorg. Chem. 1995, 34, 5753-5760.
19. Hydroperoxides such as tert-butyl hydroperoxide are known to serve as the oxygen source for POM-catalyzed oxidations; however, these epoxidations are of limited success in view of the low reactivity and, in most cases, undesirable radical-type reactions, see: (a) Faraj, M.; Hill, C. L. J. Chem. Soc., Chem. Commun. 1987, 1487-1489. (b) Neumann, R.; Khenkin, A. M. Inorg. Chem. 1995, 34, 5753-5760.
20. (a) Adam, W.; Rao, P. B.; Degen, H.-G.; Saha-Möller, C. R. J. Am. Chem. Soc. 2000, 122, 5654-5655
21. (b) Aoki, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 187-207.
22. (a) Adam, W.; Hajra, S.; Herderich M.; Saha-Möller, C. R. Org. Lett. 2000, 2, 2773-2776
23. (b) Adam, W.; Herold, M.; Hill, C. L.; Saha-Möller, C. R. Eur. J. Org. Chem. 2002, 941-946
24. (c) Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703-710.
25. The synthesis and X-ray structure of oxovanadium(IV) POM is known; see: Tourné, C. M.; Tourné, G. F.; Zonnevijlle, F. J. Chem. Soc., Dalton Trans. 1991, 143-155.
26. Only primary allylic alcohols were used because kinetic resolution of racemic secondary allylic alcohols has been shown to give poor results in metal-catalyzed asymmetric epoxidations, see: (a) Adam, W.; Humpf, H.-U.; Roschmann, K. J.; Saha-Möller, C. R. J. Org. Chem. 2001, 66, 5796-5800. (b) Adam, W.; Prikhodovski, S.; Roschmann, K. J.; Saha-Möller, C. R. Tetrahedron: Asymmetry 2001, 12, 2677-2681.
27. Only primary allylic alcohols were used because kinetic resolution of racemic secondary allylic alcohols has been shown to give poor results in metal-catalyzed asymmetric epoxidations, see: (a) Adam, W.; Humpf, H.-U.; Roschmann, K. J.; Saha-Möller, C. R. J. Org. Chem. 2001, 66, 5796-5800. (b) Adam, W.; Prikhodovski, S.; Roschmann, K. J.; Saha-Möller, C. R. Tetrahedron: Asymmetry 2001, 12, 2677-2681.
28. (a) Villa, A. L.; De Vos, D. E.; Verpoort, F.; Sels, B. F.; Jacobs, P. A. J. Catal. 2001, 198, 223-231.
29. (b) Haanepen, M. J.; Van Hooff, J. H. C. Appl. Catal. A 1997, 152, 183-201.
30. (c) Haanepen, M. J.; Elemans-Mehring, A. M.; Van Hooff, J. H. C. Appl. Catal. A 1997, 152, 203-219.
31. (S)-(-)-(1-Phenyl)ethyl hydroperoxide was prepared by enzymatic kinetic resolution according to the literature procedure: Adam, W.; Hoch, U.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. J. Am. Chem. Soc. 1995, 117, 11898-11901.
32. The resulting TADDOL was recovered in >95% yield by silica gel chromatography without loss of optical purity, from which TADOOH may be easily regenerated, see ref 7b.
33. 2 as oxygen source revealed that the substituting transition metals are not directly involved in the oxygen-transfer process, see refs 3g and 3h.
34. (a) Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136-6137.
35. (b) Michaelson, R. C.; Palermo, R. E.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 1990-1992.
36. (c) Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63-73.
37. Vogl, N. Diplomarbeit, University of Würzburg, Germany, 2002.
38. It would be too speculative at this time to propose a definite structure for the vanadium(V)-centered POM template to rationalize the stereochemical course of the epoxidation.