Fungal deracemization of benzoin

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6447-6449

  Demir, Ayhan S ^a   Hamamci, Haluk ^a   Sesenoglu, Ozge ^a   Neslihanoglu, Rahsan ^a   Asikoglu, Beril ^a   Capanoglu, Doga ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Benzoin; Deracemization; Fungi; Hydroxyketones

Indexed keywords

BENZOIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; DERACEMIZATION; ENANTIOMER; NONHUMAN; PH; RHIZOPUS ORYZAE; STEREOCHEMISTRY;

FUNGI; RHIZOPUS; RHIZOPUS ORYZAE;

EID: 0037009718     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01362-X     Document Type: Article

References (36)

1. Coppola G.M., Schuster H.F. α-Hydroxy Acids in Enantioselective Synthesis. 1997;VCH, Weinheim.
2. Gala D., DiBenedetto D.J., Clark J.E., Murphy B.L., Schumacher D.P., Steinman M. Tetrahedron Lett. 37:1996;611.
3. Chaudhary A.G., Kingston D.G.I. Tetrahedron Lett. 34:1993;4921.
4. (d) Polonský, J. Forts. Chem. Org. Naturst. 1985, 47, 221;
5. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983; Chapter 2.
6. (a) Faber, K. Biotransformations in Organic Chemistry, 4th Ed.; Springer-Verlag: Berlin, 2000;
7. (b) Enzyme Catalysis in Organic Synthesis; Drauz, K.; Waldmann, H., Ed; VCH: Weinheim, 1995;
8. Wong C.H., Whitesides G.M. Enzymes in Synthetic Organic Chemistry. 1994;Pergamon, Oxford.
9. Stecher H., Faber K. Synthesis. 1996;1.
10. Caddick S., Jenkins K. Chem. Soc. Rev. 25:1996;447.
11. Ward R.S. Tetrahedron: Asymmetry. 6:1995;1475.
12. Huerta F.F., Minidis A.B.E., Backvall J.E. Chem. Soc. Rev. 30:2001;321.
13. Pesti J.A., Yin J., Zhang L., Anzalone L. J. Am. Chem. Soc. 123:2001;11075.
14. Caddick S., Jenkins K. Chem. Soc. Rev. 25:1996;447.
15. Kitamura M., Tokunaga M., Noyori R. J. Am. Chem. Soc. 115:1993;144.
16. Strauss U.T., Felfer U., Faber K. Tetrahedron: Asymmetry. 10:1999;107.
17. Kuebrich J.P., Schowen R.L., Wang M., Lupes M.E. J. Am. Chem. Soc. 93:1971;1214.
18. Stetter H., Rämsch Y., Kuhlmann H. Synthesis. 1976;733.
19. Castells J., López-Calahorra F., Domingo L. J. Org. Chem. 53:1988;4433.
20. Matsumoto T., Ohishi M., Inoue S. J. Org. Chem. 50:1985;603.
21. Knight R.L., Leeper F.J. J. Chem. Soc., Perkin Trans. 1. 1998;1891.
22. Enders D., Breuer K. Helv. Chim. Acta. 79:1996;1217.
23. Adam W., Müller M., Prechtl F. J. Org. Chem. 59:1994;2358.
24. Adam W., Fell R.T., Stegmann V.R., Saha-Möller C.R. J. Am. Chem. Soc. 120:1998;708.
25. Adam W., Saha-Moeller C.R., Zhao C.G. Tetrahedron: Asymmetry. 9:1998;4117.
26. Adam W., Fell R.T., Saha-Möller C.R., Zhao C.G. Tetrahedron: Asymmetry. 9:1998;397.
27. Adam W., Fell R.T., Hoch U., Saha-Möller C.R., Schreier P. Tetrahedron: Asymmetry. 6:1995;1047.
28. Adam W., Díaz M.T., Fell R.T., Saha-Möller C.R. Tetrahedron: Asymmetry. 7:1996;2207.
29. Demir A.S., Hamamci H., Tanyeli C., Akhmedov I.M., Doganel F. Tetrahedron: Asymmetry. 9:1998;1673.
30. Demir A.S., Hamamci H., Sesenoglu O., Capanoglu D., Neslihanoglu R. Tetrahedron: Asymmetry. 12:2001;1953.
31. Demir A.S., Sesenoglu O., Eren E., Hosrik B., Pohl M., Janzen E., Kolter D., Feldmann R., Dünkelmann P., Müller M. Adv. Synth. Catal. 344:2002;96.
32. Demir A.S., Pohl M., Janzen E., Müller M. J. Chem. Soc., Perkin Trans. 1. 2001;633.
33. Dünnwald T., Demir A.S., Siegert P., Pohl M., Müller M. Eur. J. Org. Chem. 2000;2161.
34. Demir A.S., Dünnwald T., Iding H., Pohl M., Müller M. Tetrahedron: Asymmetry. 10:1999;4769.
35. Iding H., Dünnwald T., Greiner L., Liese A., Müller M., Siegert P., Grötzinger J., Demir A.S., Pohl M. Eur. J. Chem. 6:2000;1483.
36. t (S)-benzoin: 32.27 min.