N. W. Fadnavis, K. R. Radhika / Tetrahedron: Asymmetry 15 (2004) 3443–3447
3447
1505, 1745, 2760, 3080, 3480. 1H NMR (CDCl3,
200MHz): dppm 1.28 (t, 3H, J = 7.1Hz), 1.90–2.10 (m,
4H), 2.76 (m, 2H), 2.80 (s, br, 1H), 4.2 (m, 3H), 7.15–
4. (a) Fechter, M. H.; Griengl, H., 2nd ed. In Enzyme
Catalysis in Organic Synthesis; Drauz, K., Waldman, H.,
Eds.; Wiley-VCH: Weinheim, 2002; Vol. 2, Chapter 14, p
974; (b) North, M. Tetrahedron: Asymmetry 2003, 14, 147;
(c) Wang, Y. F.; Chen, S. T.; Liu, K. K. C.; Wong, C. H.
Tetrahedron Lett. 1989, 30, 1917.
7.35 (m, 5H). 13C NMR (CDCl3, 200MHz): dppm 175,
25
D
142, 127, 128, 130, 98, 72, 63, 32, 43, 16. ½aꢁ ¼ ꢀ18:1
(c 1.0, chloroform), lit.8b ꢀ20.8 (c 1.0, chloroform).
5. Osprian, I.; Fechter, M. H.; Griengl, H. J. Mol. Catal. B:
Enzym. 2003, 24-25, 89.
4.8. Reverse phase HPLC analysis
6. (a) Kalaritis, P.; Regenye, R. W.; Oartridge, J. J.; Coffen,
D. L. J. Org. Chem. 1990, 55, 812; (b) Liese, A.; Kragl, U.;
Kierkels, H.; Schulze, B. Enzyme Microbiol. Technol. 2002,
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Enzym. 2004, 28, 65; (d) Sugai, T.; Ohta, H. Agric. Biol.
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7. Chadha, A.; Baskar, B. Tetrahedron: Asymmetry 2002, 13,
1461.
The disappearance of dioxo ester 4b was followed by re-
verse phase HPLC. Column C-18 (250 · 5mm), Chrom-
pack, The Netherlands. Mobile phase 70% acetonitrile–
water containing 0.2% formic acid. Flow rate 0.7mL/
min. Detection wavelength 316nm. Retention times 4b:
9.3min, 4a: 8.2min. The product profile was analyzed
on the same column at 246nm with a mobile phase of
40% acetonitrile–water containing 0.2% formic acid.
Retention times: 5b: 10.4min, 5a: 5.4min, 8: 7.0min.
8. (a) Herold, P.; Indolese, A. F.; Studer, M.; Jalett, H. P.;
Siegrist, U.; Blaser, H. U. Tetrahedron 2000, 56, 6497; (b)
Blaser, H. U.; Burkhardt, S.; Kirner, H. J.; Mossner, T.;
Studer, M. Synthesis 2003, 1679.
4.9. HPLC with chiral stationary phase
9. Dao, D. H.; Okamura, M.; Akasaka, T.; Kawai, Y.; Hida,
K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 2725.
10. (a) Casy, G. Tetrahedron Lett. 1992, 33, 8159; (b) Casey,
G.; Lee, T.; Lee, V.; Lee, E. A. U.S. Patent 5,686,275,
1997.
11. (a) Nakamura, K.; Yamanaka, R.; Matsuda, T.; Harada,
T. Tetrahedron: Asymmetry 2003, 14, 2659; (b) Csuk, R.;
Glanzer, B. I. In Stereoselective Biocatalysis; Patel, R. N.,
Ed.; Dekker: New York, 2000; p 527; (c) Csuk, R.;
Glanzer, B. I. Chem. Rev. 1991, 91, 49–97; (d) DÕArrigo,
P.; Pedrocchi-Fantoni, G.; Servi, S. In Stereoselective
Biocatalysis; Patel, R. N., Ed.; Dekker: New York, 2000; p
365; (e) DÕArrigo, P.; Pedrocchi-Fantoni, G.; Servi, S.
Adv. Appl. Microbiol. 1997, 44, 81.
Enantiomeric excesses were determined by HPLC anal-
ysis on Chiralcel OD column (250 · 5mm), Daicel
Chemical Industries, Japan. Mobile phase 10% isopro-
pyl alcohol in hexane containing 0.1% trifluoroacetic
acid; flow rate 0.7mL/min. Compound 5b: detection
wavelength 246nm; retention times: (R)-hydroxyester
20.5min; (S)-hydroxyester 19.1min; 6: detection wave-
length 254nm; retention times: (R)-hydroxyester
11.1min; (S)-hydroxyester 8.5min.
Acknowledgements
12. (a) Baraldi, P. G.; Manfredini, S.; Pollini, G. P.; Romag-
noli, R.; Simoni, D.; Zanirato, V. Tetrahedron Lett. 1992,
33, 2871; (b) Chang, C. Y.; Yang, T. K. Tetrahedron:
Asymmetry 2003, 14, 2239; (c) Kaluzna, I.; Andrew, A. A.;
Bonilla, M.; Martzen, M. R.; Stewart, J. D. J. Mol. Catal.
B: Enzym. 2002, 17, 101.
We thank CSIR, New Delhi, India for the grant of SRF
to K.R.R. and financial assistance.
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