Position and enantioselective dihydroxylation of 2-hydroxymethyl-and 2-hydroxyethyl-1,3-butadiene derivatives using bis-cinchona alkaloid catalysts

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1739-1742

  Noe, Mark C ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA;

1,3 BUTADIENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HYDROXYLATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029986719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00162-1     Document Type: Article

References (26)

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. (e) Corey, E. J.; Noe, M. C.; Ting, A. Y., preceding paper.
6. Although the dihydroxylation of terminal allylic alcohols proceeds with poor enantioselectivity, it has been shown that reaction of tertiary or cis-allylic alcohols can proceed with good levels of enantioselectivity: (a) Wang, Z.-M.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 8225,
7. (b) VanNieuwenhze, M. S.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 843 and
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. (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.
10. 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.
11. 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 and
12. (c) Byun, H.-S.; Kumar, E. R.; Bittman, R. J. Org. Chem. 1994, 59, 2630.
13. (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
14. (b) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Letters 1994, 35, 2861.
15. (c) Corey, E. J.; Noe, M. C.; Sarshar, S. J. Am. Chem. Soc. 1993, 115, 3828.
16. (d) Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1994, 35, 6427.
17. For leading references to methods for the position selective dihydroxylation of polyunsaturated substrates using the Sharpless asymmetric dihydroxylation, see (a) Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron, 1995, 57, 1345.
18. (b) Corey, E. J.; Noe, M. C.; Lin, S. Tetrahedron Lett. 1995, 36, 8741.
19. Compounds 5a, 5b and 5 e were prepared from the corresponding known allylic alcohols. See (a) Barluenga, J.; Fernández-Simón, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc. Perkin Trans. 1 1989, 77.
20. (b) Frangin, Y.; Gaudemar, M. J. Organomet. Chem. 1977, 142, 9.
21. 3 in methanol, followed by coupling with 3.0 equiv of p-methoxyphenol, 1.3 equiv of PPh3 and 1.3 equiv of diethylazodicarboxylate in THF at reflux for 2 h to give 5d in 85% yield. See (c) Fukuyama, T.; Laird, A. A.; Hotchkiss, L. M. Tetrahedron Lett. 1985, 26, 6291.
22. For conformational studies of allylic systems, see (a) Bothner-By, A. A.; Castellano, S.; Ebersole, S. J.; Günther, H. J. Am. Chem. Soc. 1966, 88, 2466.
23. (b) Gung, B. W.; Wolf, M. A.; Zhu, Z. J. Org. Chem. 1993, 58, 3350.
24. (c) Gung, B. W.; Wolf, M. A. J. Org. Chem. 1993, 58, 7038.
25. A theoretical treatment appears in (d) Wiberg, K. B.; Martin, E. J. Am. Chem. Soc. 1985, 707, 5035.
26. This research was assisted financially by a graduate fellowship to M.C.N. (NSF) and a grant from the National Science Foundation.