A highly diastereoselective electrochemical epoxidation

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 777-778

  Rossen, K ^a   Volante, R P ^a   Reider, P J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDINAVIR;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS;

EID: 0031025474     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02445-8     Document Type: Article

References (16)

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2. (b) Little, R.D.; Weinberg, N.L. Electroorganic Synthesis, Dekker, New York, 1991
3. (c) Gorny, R.; Schäfer, HJ.; Fröhlich, R. Angew. Chem. Int. Ed. Engl. 1995, 34, 189.
4. (d) Torii, S.; Tanaka, H.; Inokuchi, T. Top. Curr. Chem. 1988, 148, 153.
5. (a) Vacca, J.P.; Dorsey, B.D.; Schleif, W.A.; Levin, R.B.; McDaniel, S.L.; Darke, P.L.; Zugay, J.; Quintero, J.C.; Blahy, O.M.; Sardana, V.V.; Schlabach, A.J.; Graham, P.I.; Condra, J.H.; Gotlib, L.; Holloway, M.K.; Lin, J.; Chen, I.-W.; Vastag, K.; Ostovic, D.; Andersen, P.S.; Emini, E.A.; Huff, J.R. Proc. Natl. Acad. Sci. USA 1994, 91, 4096.
6. (b) Idem., J. Med. Chem. 1994, 37, 3443.
7. (c) Askin, D.; Eng, K.K.; Rossen, K.; Purick, R.M.; Wells, K.M.; Volante, R.P.; Reider, P.J. Tetrahedron Lett. 1994, 35, 673.
8. Rossen, K.; Weissman, S.A.; Sager, J.; Reamer, R.A.; Askin, D.A.; Volante, R.P.; Reider, P.J. Tetrahedron Lett. 1995, 36, 6419.
9. (a) Maligres, P.E.; Upadhyay, V.; Rossen, K.; Cianciosi, S.J.; Purick, R.M.; Eng, K.K.; Reamer, R.A.; Askin, D.; Volante, R.P.; Reider, P.J. Tetrahedron Lett. 1995, 36, 2195.
10. (b) Maligres, P.E.; Weissman, S.A.; Upadhyay, V.; Cianciosi, S.J.; Reamer, R.A.; Purick, R.M.; Sager, J.; Rossen, K.; Eng, K.K.; Askin, D.; Volante, R.P.; Reider, P.J. Tetrahedron 1996, 52, 3327.
11. Previous examples for the electrochemical epoxidation of simple olefins: (a) Scott, K.; Odoza, C.; Hui, W. Chem. Eng. Res. Des. 1995, 73(A3), 330.
12. (b) Torii, S.; Uneyama, K.; Tanka, H.; Yamanaka, T.; Yasuda, T.; Ono, M.; Kohmoto, Y. J. Org. Chem. 1981, 46, 3312.
13. 2O 40/60 assay, ImL/min, RT 1 12.4 min, RT 4b 13.5 min.
14. 2 and HgO reacts with 3 to give 4b in 84 % yield.
15. An interesting dependence of the diastereoselectivity and isolated yield on the stoichiometry of the NaBr was noted: 0.5 equiv. NaBr, 89% yield, 93:7 de 1.0 equiv. NaBr, 86% yield, 94:6 de 2.0 equiv. NaBr, 80% yield, 97:3 de
16. Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry, John Wiley, New York, 1988 page 563 ff.