Enzyme Mediated Synthesis of Stereoisomerically Pure α,ω-Diepoxides

Synlett

Volumn 1996, Issue 7, 1996, Pages 615-616

  Hoye, Thomas R ^a   Tan, Lushi ^a  

^a University of Minnesota ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343776276     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5578     Document Type: Article

References (27)

1. Dow Graduate Fellow, 1993-94.
2. (a) Schreiber, S. L. Chem. Scripta 1987, 27, 563.
3. (b) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120.
4. (c) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15.
5. (d) Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J. Org. Chem. 1991, 56, 5161.
6. Sharpless, K. B.; Amberg, W.; Bennani, Y.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
7. Kolb, H.; Sharpless, K. B. Tetrahedron 1992, 48, 10515.
8. (a) Wallace, T. S.; Baldwin, G. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231.
9. (b) Takemura, T.; Saito, K.; Nakazawa, S.; Mori, N. Tetrahedron Lett. 1992, 33, 6335.
10. (c) Nagai, H.; Morimoto, T.; Achiwa, K. Synlett 1994, 289.
11. (d) Caron, G.; Kazlauskas, R. J. Tetrahedron Asymmetry 1994, 5, 657.
12. (e) Chenevert, R.; Desjardins, M. J. Org. Chem. 1996, 61, 1219.
13. Haase, B.; Schneider, M. P. Tetrahedron Asymmetry 1993, 4, 1017.
14. (a) Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 6421.
15. (b) Degueil-Castaing, M.; Jeso, B. D.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953.
16. (c) Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 3127.
17. (d) Fang, J.-M.; Wong, C.-H. Synlett 1994, 393.
18. (e) Klibanov, A. M. CHEMTECH 1986, 354.
19. (f) Empie, M. W.; Gross, A. Ann. Rep. Med. Chem. 1988, 23, 305.
20. (g) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
21. (h) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: New York, 1994; Chapter 2.
22. Use of SP-435 (Johnson, C. R.; Bis, S. J. Tetrahedron Lett. 1992, 33, 7287) as catalyst for the transesterification reaction of substrates 13a and 13b was not convenient. It was considerably slower than the reactions using PS-30. Moreover, the simple substrate (±)-1-tert-butylthio-2-octanol gave product of only marginal %ee when esterified with vinyl acetate and SP-435.
23. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
24. 1H NMR analysis of all the Mosher esters shown here, see Tan, L. Ph. D. Dissertation, University of Minnesota, 1995.
25. 1H NMR spectra of diastereomeric compounds 21a and 23a (or 21b and 23b) even though the configuration of the remote acetoxy-bearing stereocenter is opposite. The same situation was observed in the spectra of the diastereomeric pairs 22/24.
26. (b) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Org. Chem. 1992, 57, 3631. (Equation Presented)
27. Goergens, U.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 1065.