Improved enantioselective dihydroxylation of bishomoallylic alcohol derivatives using a mechanistically inspired bis-cinchona alkaloid catalyst

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1735-1738

  Corey, E J ^a   Noe, Mark C ^a   Ting, Alice Y ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID ESTER DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

CINCHONA;

EID: 0029964126     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00163-3     Document Type: Article

References (18)

1. (a) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 12109.
2. (b) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. Tetrahedron Lett. 1995, 36, 3481.
3. (c) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805.
4. (d) Corey, E. J.; Noe, M. C.; Guzman-Perez, A. J. Am. Chem. Soc. 1995, 117, 10817.
5. In contrast to the dihydroxylation of terminal allylic alcohols which proceeds with poor enantioselectivity, the reaction of allylic alcohols with internal E-double bonds can proceed with good levels of enantioselectivity: (a) Wang, Z.-M.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 8225.
6. (b) VanNieuwenhze, M. S.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 843.
7. (c) Xu, D.; Park, C. Y.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 2495. For a recent review, see Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
8. (c) Xu, D.; Park, C. Y.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 2495. For a recent review, see Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
9. The dihydroxylation of a series of substituted allyl aryl ethers has been reported to give products with ee's averaging 70%; see: (a) Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 2267.
10. On the other hand, allyl p-methoxyphenyl ether afforded the corresponding diol of 90-92% ee. See: (b) Vilchèze, C.; Bittman, R. J. Lipid Res. 1994, 35, 734
11. (c) Byun, H.-S.; Kumar, E. R.; Bittman, R. J. Org. Chem. 1994, 59, 2630.
12. (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
13. (b) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861.
14. (c) Corey, E. J.; Noe, M. C.; Sarshar, S. J. Am. Chem. Soc. 1993, 115, 3828.
15. (d) Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1994, 35, 6427.
16. For conformational studies of cinchona alkaloid derivatives, see Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
17. 3 in methanol. See Partridge, J. J.; Shiuey, S.-J.; Chadha, N. K.; Baggiolini, E. G.; Blount, J. F.; Uskokovic, M. R. J. Am. Chem. Soc. 1981, 103, 1253.
18. This research was assisted financially by a graduate fellowship to M.C.N. (NSF), an undergraduate research fellowship to A.Y.T. (Pfizer), and a grant from the National Science Foundation.