Non-Racemic Halohydrins via Biocatalytic Hydrogen-Transfer Reduction
FULL PAPERS
(1S,2S)-6b, ee>98%, [a]J25: þ122 (CHCl3, c 0.03). (1R,2S)-6b,
ee>99%, [a]2D0: À40 (CHCl3, c 0.5), [a]J20: À75 (CHCl3, c 0.5),
ref.[29] (1R,2S)-6b, ee>98%, [a]j25: À80 (CHCl3, c 0.03).
The absolute configuration of 4b was determined by co-in-
jection on chiral GC with independently obtained enantiopure
reference material. The absolute configuration of 5b was deter-
mined by comparison of the elution order on chiral GC with lit-
erature values.[62]
[18] N. Kizaki, Y. Yasohara, J. Hasegawa, M. Wada, M. Ka-
taoka, S. Shimizu, Appl. Microbiol. Biotechnol. 2001,
55, 590–595.
[19] Y. Yasohara, N. Kizaki, J. Hasegawa, M. Wada, M. Ka-
taoka, S. Shimizu, Tetrahedron: Asymmetry 2001, 12,
1713–1718.
[20] A. Matsuyama, H. Yamamoto, N. Kawada, Y. Kobayashi,
J. Mol. Catal. B: Enzym. 2001, 11, 513–521.
[21] H. Yamamoto, K. Mitsuhashi, N. Kimoto, A. Matsuya-
ma, N. Esaki, Y. Kobayashi, Biosci. Biotechnol. Biochem.
2004, 68, 638–649.
For GC data of all compounds see Supporting Information.
Acknowledgements
[22] O. Cabon, D. Buisson, M. Larcheveque, R. Azerad, Tet-
rahedron: Asymmetry 1995, 6, 2211–2218.
This study was performed within the Spezialforschungsbereich
“Biokatalyse” and the Research Centre Applied Biocatalysis.
Financial support by CIBASC (Basel), Fonds zur Fçrderung
der wissenschaftlichen Forschung (Vienna, project no. F115),
TIG, SFG, Province of Styria and City of Graz is gratefully ac-
knowledged. We are indebted to CIBASC for the generous don-
ation of compounds 4a and 4b.
[23] A. Goswami, R. L. Bezbaruah, J. Goswami, N. Bortha-
kur, D. Dey, A. K. Hazarika, Tetrahedron: Asymmetry
2000, 11, 3701–3709.
[24] E. P. S. Filho, J. A. R. Rodrigues, P. J. S. Moran, J. Mol.
Catal. B: Enzym. 2001. 15, 23–28.
[25] F. M. Lagos, C. Del Campo, E. F. Llama, J. V. Sinisterra,
Enzyme Microb. Technol. 2002, 30, 895–901.
[26] A. Goswami, K. D. Mirfakhrae, M. J. Totleben, S. Swa-
minathan, R. N. Patel, J. Ind. Microbiol. Biotechnol.
2001, 26, 259–262.
References
[27] K. Nakamura, R. Yamanaka, T. Matsuda, T. Harada, Tet-
rahedron: Asymmetry 2003, 14, 2659–2681.
[28] K. Nakamura, T. Matsuda, J. Org. Chem. 1998, 63, 8957–
8964.
[29] P. Besse, M. F. Renard, H. Veschambre, Tetrahedron:
Asymmetry 1994, 5, 1249–1268.
[30] P. Besse, T. Sokoltchik, H. Veschambre, Tetrahedron:
Asymmetry 1998, 9, 4441–4457.
[31] F. M. Lagos, J. D. Carballeira, J. L. Bermudez, E. Alvar-
ez, J. V. Sinisterra, Tetrahedron: Asymmetry 2004, 15,
763–770.
[32] J. D. Carballeira, E. Alvarez, M. Campillo, L. Pardo, J. V.
Sinisterra, Tetrahedron: Asymmetry 2004, 15, 951–962.
[33] R. Imashiro, M. Seki, J. Org. Chem. 2004, 69, 4216–4226.
[34] W. Stampfer, B. Kosjek, C. Moitzi, W. Kroutil, K. Faber,
Angew. Chem. Int. Ed. 2002, 41, 1014–1017.
[35] W. Stampfer, B. Kosjek, W. Kroutil, K. Faber, (Ciba Spe-
ciality Chemicals Holding Inc.), World Patent WO 03/
078615 A1, 2003; Chem. Abstr. 2003, 139, 272906.
[36] W. Stampfer, B. Kosjek, K. Faber, W. Kroutil, J. Org.
Chem. 2003, 68, 402–406.
[37] B. Kosjek, W. Stampfer, M. Pogorevc, W. Goessler, K.
Faber, W. Kroutil, Biotechnol. Bioeng. 2004, 86, 55–62.
[38] V. Prelog, Pure Appl. Chem. 1964, 9, 119–130.
[39] P. Hildebrandt, A. Musidlowska, U. T. Bornscheuer, J.
Altenbuchner, Appl. Microbiol. Biotechnol. 2002, 59,
483–487.
[40] P. Hildebrandt, T. Riermeier, J. Altenbuchner, U. T.
Bornscheuer, Tetrahedron: Asymmetry 2001, 12, 1207–
1210.
[41] M. L. F. Cadman, L. Crombie, S. Freeman, J. Mistry, J.
Chem. Soc. Perkin. Trans. 1 1995, 11, 1397–1407.
[42] R. D. Riecke, J. D. Brown, X. Wu, Synth. Commun. 1995,
25, 3923–3930.
[1] I. Izquierdo, M. T. Plaza, M. Rodriguez, J. A. Tamajo, A.
Martos, Tetrahedron: Asymmetry 2001, 12, 293–300.
[2] H. Hamada, T. Miura, H. Kumobayashi, T. Matsuda, T.
Harada, K. Nakamura, Biotechnol. Lett. 2001, 23,
1603–1606.
[3] M. Chartrain, R. Greasham, J. Moore, P. Reider, D. Rob-
inson, B. Buckland, J. Mol. Catal. B: Enzym. 2001, 11,
503–512.
[4] A. Kamal, R. B. Khanna, T. Krishnaji, Tetrahedron Lett.
2003, 44, 4783–4787.
[5] E. Sundby, J. Holt, A. Vik, T. Anthonsen, Eur. J. Org.
Chem. 2004, 1239–1243.
[6] U. Ader, M. P. Schneider, Tetrahedron: Asymmetry 1992,
3, 521–524.
[7] F. Martinez, C. Del Campo, J. V. Sinisterra, E. F. Llama,
Tetrahedron: Asymmetry 2000, 11, 4651–4660.
[8] R. N. Patel, Enzyme Microb. Technol. 2002, 31, 804–826.
[9] R. N. Patel, L. Chu, R. Mueller, Tetrahedron: Asymmetry
2003, 14, 3105–3109.
[10] R. Hett, R. Stare, P. Helquist, Tetrahedron Lett. 1994, 35,
9375–9378.
[11] T. Hamada, T. Torii, K. Izawa, R. Noyori, T. Ikariya, Org.
Lett. 2002, 4, 4373–4376.
[12] T. Zelinski, J. Peters, M.-R. Kula, J. Biotechnol. 1994, 33,
283–292.
[13] I. A. Kaluzna, T. Matsuda, A. K. Sewell, J. D. Stewart, J.
Am. Chem. Soc. 2004, 126, 12827–12832.
[14] M. Wolberg, I. A. Kaluzna, M. Müller, J. D. Stewart, Tet-
rahedron: Asymmetry 2004, 15, 2825–2828.
[15] I. A. Kaluzna, B. D. Feske, W. Wittayanan, I. Ghiviriga,
J. D. Stewart, J. Org. Chem. 2005, 70, 342–45.
[16] T. Schubert, W. Hummel, M. Müller, Angew. Chem. Int.
Ed. 2002, 41, 634–637.
[17] C. W. Bradshaw, H. Fu, G.-J. Shen, C.-H. Wong, J. Org.
Chem. 1992, 57, 1526–1532.
[43] L. Zhu, R. M. Wehmeyer, R. D. Rieke, J. Org. Chem.
1991, 56, 1445–1453.
Adv. Synth. Catal. 2005, 347, 1827 – 1834
ꢁ 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
1833