Vanadium-catalyzed asymmetric oxidation of α-hydroxy esters using molecular oxygen as stoichiometric oxidant

Journal of the American Chemical Society

Volumn 127, Issue 4, 2005, Pages 1090-1091

  Radosevich, Alexander T ^a   Musich, Christine ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYACID; ESTER; OXYGEN; VANADIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPOXIDATION; ETHERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STEREOCHEMISTRY; STEREOISOMERISM; STOICHIOMETRY; SYNTHESIS;

EID: 13644257677     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0433424     Document Type: Article

References (37)

1. For general discussions, see: (b) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Ed.; Wiley & Sons: New York, 1988; Vol. 18, pp 249-330. (b) Kieth J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5. (c) Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 489.
2. For general discussions, see: (b) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Ed.; Wiley & Sons: New York, 1988; Vol. 18, pp 249-330. (b) Kieth J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5. (c) Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 489.
3. For general discussions, see: (b) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Ed.; Wiley & Sons: New York, 1988; Vol. 18, pp 249-330. (b) Kieth J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5. (c) Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 489.
4. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
5. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
6. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
7. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
8. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
9. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
10. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
11. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
12. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
13. For alternative enantioselective synthesis of α-hydroxy esters by carbonylene reaction: (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky. T. J. Am. Chem. Soc. 2000, 122, 7936. (b) Kikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (c) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937. Friedel-Crafts reaction: (c) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146. Aldol addition: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Addition of dialkylzinc reagents: (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668. Asymmetric hydrogenation: (g) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Susumu, A.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (h) Garland, M.; Blaser, H. U. J. Am. Chem. Soc. 1990, 112, 7048. (i) LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun, Y.-K. J. Am. Chem. Soc. 1999, 121, 4920.
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