A. S. Demir et al. / Tetrahedron Letters 43 (2002) 6447–6449
6449
Acknowledgements
7. (a) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin
Trans. 1 1998, 1891; (b) Enders, D.; Breuer, K. Helv.
Chim. Acta 1996, 79, 1217.
The financial support of the Scientific and Technical
Research Council of Turkey (TUBITAK), the Turkish
State Planning Organization (for GC-LC MS) and
Middle East Technical University (AFP 2001) are
gratefully acknowledged.
8. (a) Adam, W.; M u¨ ller, M.; Prechtl, F. J. Org. Chem.
1994, 59, 2358; (b) Adam, W.; Fell, R. T.; Stegmann, V.
R.; Saha-M o¨ ller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
9. (a) Adam, W.; Saha-Moeller, C. R.; Zhao, C. G. Tetra-
hedron: Asymmetry 1998, 9, 4117; (b) Adam, W.; Fell, R.
T.; Saha-M o¨ ller, C. R.; Zhao, C. G. Tetrahedron: Asym-
metry 1998, 9, 397; (c) Adam, W.; Fell, R. T.; Hoch, U.;
Saha-M o¨ ller, C. R.; Schreier, P. Tetrahedron: Asymmetry
References
1
995, 6, 1047; (d) Adam, W.; D ´ı az, M. T.; Fell, R. T.;
Saha-M o¨ ller, C. R. Tetrahedron: Asymmetry 1996, 7,
207.
1
. (a) Coppola, G. M.; Schuster, H. F. h-Hydroxy Acids in
Enantioselective Synthesis; VCH: Weinheim, 1997; (b)
Gala, D.; DiBenedetto, D. J.; Clark, J. E.; Murphy, B.
L.; Schumacher, D. P.; Steinman, M. Tetrahedron Lett.
2
1
0. (a) Demir, A. S.; Hamamci, H.; Tanyeli, C.; Akhmedov,
I. M.; Doganel, F. Tetrahedron: Asymmetry 1998, 9,
1
Capanoglu, D.; Neslihanoglu, R. Tetrahedron: Asymme-
try 2001, 12, 1953.
1
996, 37, 611; (c) Chaudhary, A. G.; Kingston, D. G. I.
673; (b) Demir, A. S.; Hamamci, H.; Sesenoglu, O.;
Tetrahedron Lett. 1993, 34, 4921; (d) Polonsk y´ , J. Forts.
Chem. Org. Naturst. 1985, 47, 221; (e) Hanessian, S.
Total Synthesis of Natural Products: The Chiron
Approach; Pergamon Press: New York, 1983; Chapter 2.
. (a) Faber, K. Biotransformations in Organic Chemistry,
1
1. (a) Demir, A. S.; Sesenoglu, O.; Eren, E.; Hosrik, B.;
Pohl, M.; Janzen, E.; Kolter, D.; Feldmann, R.; D u¨ nkel-
mann, P.; M u¨ ller, M. Adv. Synth. Catal. 2002, 344, 96;
2
4
th ed.; Springer-Verlag: Berlin, 2000; (b) Enzyme Cataly-
(
b) Demir, A. S.; Pohl, M.; Janzen, E.; M u¨ ller, M. J.
sis in Organic Synthesis; Drauz, K.; Waldmann, H., Ed;
VCH: Weinheim, 1995; (c) Wong, C. H.; Whitesides, G.
M. Enzymes in Synthetic Organic Chemistry; Pergamon:
Oxford, 1994; (d) Stecher, H.; Faber, K. Synthesis 1996,
Chem. Soc., Perkin Trans. 1 2001, 633; (c) D u¨ nnwald, T.;
Demir, A. S.; Siegert, P.; Pohl, M.; M u¨ ller, M. Eur. J.
Org. Chem. 2000, 2161; (d) Demir, A. S.; D u¨ nnwald, T.;
Iding, H.; Pohl, M.; M u¨ ller, M. Tetrahedron: Asymmetry
1; (e) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25,
447; (f) Ward, R. S. Tetrahedron: Asymmetry 1995, 6,
1475; (g) Huerta, F. F.; Minidis, A. B. E.; Backvall, J. E.
1999, 10, 4769; (e) Iding, H.; D u¨ nnwald, T.; Greiner, L.;
Liese, A.; M u¨ ller, M.; Siegert, P.; Gr o¨ tzinger, J.; Demir,
A. S.; Pohl, M. Eur. J. Chem. 2000, 6, 1483.
Chem. Soc. Rev. 2001, 30, 321.
1
2. pH values of the reactions were adjusted using 1N NaOH
solution and lactic acid solution. After the reaction was
complete, the fungal biomass was filtered off and the
mixture was extracted two times with 200 ml of ether.
The combined organic layers were washed with brine,
3
. (a) Pesti, J. A.; Yin, J.; Zhang, L.; Anzalone, L. J. Am.
Chem. Soc. 2001, 123, 11075; (b) Caddick, S.; Jenkins, K.
Chem. Soc. Rev. 1996, 25, 447; (c) Kitamura, M.; Toku-
naga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144.
. Strauss, U. T.; Felfer, U.; Faber, K. Tetrahedron: Asym-
metry 1999, 10, 107.
4
5
6
dried over MgSO and the crude product was purified by
4
flash column chromatography (1:8 EtOAc:hexane). All
physical and chemical properties of benzoins were identi-
cal with commercially available materials. Ee values were
determined by HPLC using a chiral column; Chiralpak
AD column, UV detection at 254 nm, eluent: hexane/2-
. Kuebrich, J. P.; Schowen, R. L.; Wang, M.; Lupes, M. E.
J. Am. Chem. Soc. 1971, 93, 1214.
. (a) Stetter, H.; R a¨ msch, Y.; Kuhlmann, H. Synthesis
1
976, 733; (b) Castells, J.; L o´ pez-Calahorra, F.;
Domingo, L. J. Org. Chem. 1988, 53, 4433; (c) Mat-
sumoto, T.; Ohishi, M.; Inoue, S. J. Org. Chem. 1985, 50,
−
1
propanol=9:1, flow 0.80 mL min 20°C. R
25.75 min, R (S)-benzoin: 32.27 min.
(R)-benzoin:
t
6
03.
t