Asymmetric aminohydroxylation of vinsylfuran

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2984-2985

  Bushey, Mark L ^a   Haukaas, Michael H ^a   O'Doherty, George A ^a  

^a University of Minnesota ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STYRENE; UNCLASSIFIED DRUG; VINYLFURAN;

ARTICLE; CATALYSIS; CHROMATOGRAPHY; ENANTIOMER; HYDROXYLATION; METHODOLOGY; OXIDATION; SYNTHESIS;

EID: 0033617464     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990095r     Document Type: Article

References (32)

1. For an excellent review of the subject, see: Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105.
2. Shono, T.; Matsumura, Y.; Tsubata, J. Chem. Lett. 1981, 1121.
3. Ben-Ishai, D.; Sataty, I.; Bernstein, Z. Tetrahedron Lett. 1976, 32, 1571.
4. (a) Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595.
5. (b) Yang, C. F.; Xu, Y. M.; Liao, L. X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227.
6. (c) See ref 1.
7. Drueckhammer, D. G.; Barbas, C. F., III; Nozaki, K.; Wong, C.-H.; Wood, C. Y.; Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607.
8. Xu, Y. M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461.
9. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
10. Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982.
11. (a) Sharpless, K. B.; Patrick, D. W.; Truesdale, L. K.; Biller, S. A. J. Am. Chem. Soc. 1975, 97, 2305.
12. (b) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
13. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
14. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507.
15. Dress, K. R.; Gossen, L. J.; Liu, H.; Jerina, D. M.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 7669.
16. Haukaas, M. H.; O'Doherty, G. A. Abstracts of Papers, 216th National Meeting of the American Chemical Society, Boston, MA, Aug 23-27, 1998; American Chemical Society: Washington, D.C., 1998; ORGN 369.
17. This in situ use of vinylfuran allows for much higher yields of diol 6. Wittig technology provides vinylfuran in yields on the order of 10%. A previous approach to vinylfuran involves a four-step sequence from furfural that involves a stoichiometric Cu-mediated decarboxylation of 3-furylpropanoic acid, see: Schmidt, U.; Werner, J. Synthesis 1986, 986.
18. At a smaller scale, the level of enantioinduction has been as high as 94%, as determined by Mosher ester analysis.
19. This procedure was carried out with a slight excess of TBSCl compared to the primary alcohol and typically afforded less that 1% of the silyl-protected secondary alcohol.
20. This lower yield may be due to over-oxidation of the furan ring. We have observed that excess nitrene source or longer reaction times leads to furan oxidation.
21. These reactions were run to 70% conversion because of our concerns of oxidation of the furan ring (ref 18) and to prevent a ligandless background reaction.
22. In addition to various electron rich styrene derivatives, excellent regioselectivity is observed in the aminohydroxylation of α,β-unsaturated esters. For cinnamates, see: (a) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507. (c) Also ref 9b. (d) For nonaromatic α,β-unsaturated esters, see: Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045- 2048.
23. In addition to various electron rich styrene derivatives, excellent regioselectivity is observed in the aminohydroxylation of α,β-unsaturated esters. For cinnamates, see: (a) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507. (c) Also ref 9b. (d) For nonaromatic α,β-unsaturated esters, see: Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045- 2048.
24. In addition to various electron rich styrene derivatives, excellent regioselectivity is observed in the aminohydroxylation of α,β-unsaturated esters. For cinnamates, see: (a) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507. (c) Also ref 9b. (d) For nonaromatic α,β-unsaturated esters, see: Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045- 2048.
25. In addition to various electron rich styrene derivatives, excellent regioselectivity is observed in the aminohydroxylation of α,β-unsaturated esters. For cinnamates, see: (a) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507. (c) Also ref 9b. (d) For nonaromatic α,β-unsaturated esters, see: Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045-2048.
26. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1975, 38, 2143.
27. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
28. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
29. (a) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810.
30. (b) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
31. (c) Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 3667.
32. (d) O'Brien, P.; Osborne, S. A.; Parker, D. D. Tetrahedron Lett. 1998, 39, 4099.