Rhodium-catalyzed asymmetric alcoholysis and aminolysis of oxabenzonorbornadiene: A new enantioselective carbon-heteroatom bond forming process [8]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5650-5651

  Lautens, Mark ^a   Fagnou, Keith ^a   Rovis, Tomislav ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBON; ORGANOBORON DERIVATIVE; OXABENZONORBORNADIENE; RHODIUM; UNCLASSIFIED DRUG;

ALKYLATION; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS ISOMER; DEGRADATION; ENANTIOMER; LETTER; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; TRANS ISOMER;

EID: 0034647227     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000134c     Document Type: Letter

References (36)

1. For a review on allylic alkylation, see: Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Springer: New York, 1999; Vol. II, p 833. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references therein. For a review on allylic amination, see: Johannsen, M.; Jorgensen, K. A.; Chem. Rev. 1998, 98, 1689 and references therein.
2. For a review on allylic alkylation, see: Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Springer: New York, 1999; Vol. II, p 833. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references therein. For a review on allylic amination, see: Johannsen, M.; Jorgensen, K. A.; Chem. Rev. 1998, 98, 1689 and references therein.
3. For a review on allylic alkylation, see: Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Springer: New York, 1999; Vol. II, p 833. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references therein. For a review on allylic amination, see: Johannsen, M.; Jorgensen, K. A.; Chem. Rev. 1998, 98, 1689 and references therein.
4. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
5. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
6. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
7. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
8. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
9. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
10. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
11. To achieve efficient catalysis with alcohol nucleophiles, intramolecular delivery of the alcohol is frequently required. For intramolecular examples, see: (a) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett. 1995, 36, 1251. (b) Thorey, C.; Wilken, J.; Henin, F.; Martens, J.; Mehler, T.; Muzart, J. Tetrahedron Lett. 1995, 36, 5527. (c) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Tetrahedron 1997, 53, 4353. (d) Storck, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073. (e) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474. For the use of tin alkoxides see: (f) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. (g) Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates as tethers, see: (h) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
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