Kinetic Resolution by Enantioselective Dihydroxylation of Secondary Allylic 4-Methoxybenzoate Esters Using a Mechanistically Designed Cinchona Alkaloid Catalyst

Journal of the American Chemical Society

Volumn 117, Issue 44, 1995, Pages 10817-10824

  Corey, E J ^a   Noe, Mark C ^a   Guzman Perez, Angel ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID ESTER DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG PURIFICATION; ENANTIOMER; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE; TECHNIQUE;

EID: 0029589632     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00149a004     Document Type: Article

References (32)

1. Corey, E.J.; Guzman-Perez, A.; Noe, M.C. J. Am. Chem. Soc. 1995, 117, 10805, Preceding paper in this issue.
2. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483.
3. Corey, E.J.; Guzman-Perez, A.; Noe, M.C. J. Am. Chem. Soc. 1994, 116, 12109.
4. Bevinakatti, H.S.; Banerji, A.A. J. Org. Chem. 1992, 57, 6003.
5. Corey, E.J.; Noe, M.C. J. Am. Chem. Soc. 1993, 115, 12579.
6. Corey, E.J.; Noe, M.C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861.
7. Corey, E.J.; Noe, M.C.; Sarshar, S. J. Am. Chem. Soc. 1993, 115, 3828.
8. Corey, E.J.; Noe, M.C.; Grogan, M.J. Tetrahedron Lett. 1994, 35, 6427.
9. VanNieuwenhze, M.S.; Sharpless, K.B. J. Am. Chem. Soc. 1993, 115, 7864.
10. Ward. R.A.; Procter, G. Tetrahedron Lett. 1992, 33, 3363.
11. Lohray. B.B.; Bhushan, V. Tetrahedron Lett. 1993, 34, 3911.
12. Hawkins, J.M.; Meyer, A. Science 1993, 260, 1918.
13. Finn, M.G.; Sharpless, K. Morrison, J.D., Ed.; Academic Press, Inc.: New York, 1985; Vol. 5, p 247.
14. Martin, V.S.; Woodard, S.S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K.B. J. Am. Chem. Soc. 1981, 103, 6237.
15. GaO, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765.
16. Crispino, G.A.; Makita, A.; Wane, Z.-M.; Sharpless, K.B. Tetrahedron Lett. 1994, 35, 543.
17. Dijkstra, G.D.H.; Kellogg, R.M.; Wynberg, H.; Svendsen, J.S.; Marko, I.; Sharpless, K.B. J. Am. Chem. Soc. 1989, 111, 8069.
18. Kolb, H.C.; Andersson, P.G.; Bennani, Y.L.; Crispino, G.A.; Jeong, K.-S.; Kwong, H.-L.; Sharpless, K.B. J. Am. Chem. Soc. 1993, 115, 12226.
19. Kagan, H.B.; Fiaud, J.C. Top. Stereochem. 1988, 18, 249.
20. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
21. Morikawa, K.; Sharpless, K.B. Tetrahedron Lett. 1993, 34, 5575.
22. Wade, P.A.; Cole, D.T.; D’Ambrosio, S.G. Tetrahedron Lett. 1994, 35, 53.
23. Jager, V.; Schroter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195.
24. Gracza, T.; Hasenohrl, T.; Stahl, U.; Jager, V. Synthesis 1991, 1108 and references cited therein.
25. Gobel, T.; Sharpless, K.B. Angew. Chem., Int. Ed. Engl. 1993, 32, 1329.
26. Kolb, H.C.; Anders son, P.G.; Sharpless, K.B. J. Am. Chem. Soc. 1994, 116, 1278.
27. Becker, H.; Ho, P.T.; Kolb, H.C.; Loren, S.; Norrby, P.-O.; Sharpless, K.B. Tetrahedron Lett. 1994, 35, 7315.
28. Norrby, P.-O.; Kolb, H.C.; Sharpless, K.B. J. Am. Chem. Soc. 1994, 116, 8470.
29. Golden, R.; Stock, L.M. J. Am. Chem. Soc. 1972, 94, 3080.
30. Corey, E.J.; Bakshi, R.K.; Shibata, S.; Chen C.-P.; Singh, V.K. J. Am. Chem. Soc. 1987, 109, 7925.
31. Mulzer, J.; Angermann, A.; Munch W.; Schlichthorl, G.; Hentzschel, A. Liebigs Ann. Chem. 1987, 7.
32. Delton, M.H.; Yuen, G.U. J. Org. Chem. 1968, 33, 2473.