Rhodium-catalyzed ring opening of vinyl epoxides with alcohols and aromatic amines

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2319-2320

  Fagnou, Keith ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012543140     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060782     Document Type: Article

References (24)

1. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Permagon Press: New York, 1991; Vol. 6.
2. For a review on allylic alkylation, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and pertinent references therein. For a review on allylic amination, see: Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689 and pertinent references therein. For a general reference on the chemistry of palladium, see: Tsuji, J. Palladium Reagents and Catalysis; Wiley and Sons Ltd.: Toronto, 1995.
3. For a review on allylic alkylation, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and pertinent references therein. For a review on allylic amination, see: Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689 and pertinent references therein. For a general reference on the chemistry of palladium, see: Tsuji, J. Palladium Reagents and Catalysis; Wiley and Sons Ltd.: Toronto, 1995.
4. For a review on allylic alkylation, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and pertinent references therein. For a review on allylic amination, see: Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689 and pertinent references therein. For a general reference on the chemistry of palladium, see: Tsuji, J. Palladium Reagents and Catalysis; Wiley and Sons Ltd.: Toronto, 1995.
5. For the use of tin alkoxides, see: Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates with alcohols, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702. For the use of carbon monoxide to give cyclic carbonates, see: Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. For the use of aldehydes to give cyclic acetals, see: Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69. For the use of isocyanates to give oxazolidinones, see: Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
6. For the use of tin alkoxides, see: Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates with alcohols, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702. For the use of carbon monoxide to give cyclic carbonates, see: Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. For the use of aldehydes to give cyclic acetals, see: Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69. For the use of isocyanates to give oxazolidinones, see: Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
7. For the use of tin alkoxides, see: Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates with alcohols, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702. For the use of carbon monoxide to give cyclic carbonates, see: Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. For the use of aldehydes to give cyclic acetals, see: Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69. For the use of isocyanates to give oxazolidinones, see: Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
8. For the use of tin alkoxides, see: Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates with alcohols, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702. For the use of carbon monoxide to give cyclic carbonates, see: Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. For the use of aldehydes to give cyclic acetals, see: Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69. For the use of isocyanates to give oxazolidinones, see: Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
9. For the use of tin alkoxides, see: Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates with alcohols, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702. For the use of carbon monoxide to give cyclic carbonates, see: Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. For the use of aldehydes to give cyclic acetals, see: Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69. For the use of isocyanates to give oxazolidinones, see: Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
10. For the use of tin alkoxides, see: Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2931. Keinan, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558. For the use of cocatalytic trialkylborates with alcohols, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702. For the use of carbon monoxide to give cyclic carbonates, see: Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. For the use of aldehydes to give cyclic acetals, see: Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69. For the use of isocyanates to give oxazolidinones, see: Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
11. Very recently, a palladium-catalyzed dynamic kinetic asymmetric transformation has been reported with phthalimide and vinyl epoxides giving the 1,2-addition products in good yield and excellent ee's. See: Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. J. Am. Chem. Soc. ASAP.
12. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
13. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
14. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
15. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
16. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
17. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
18. For use of diethylaluminum amides, see: Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 195. For use of amino silanes and stannanes, see: Papini, A.; Ricci, A.; Taddei, M. J. Chem. Soc., Perkin Trans. 1 1984, 2261. Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640. For the use of lithium, magnesium, and zinc salts, see: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661. For the use of amino lead reagents, see: Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255. For the use of cobalt-catalyzed aminolysis, see: Iqbal, J.; Pandey, A. Tetrahedron Lett. 1990, 31, 575. For the use of lanthanide catalysts, see: Fu, X.-L.; Wu, S.-H. Synth. Commun. 1997, 27, 1677.
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24. For the establishment of regio- and relative stereochemistry, see Supporting Information.