Nitrile biotransformations for highly enantioselective synthesis of oxiranecarboxamides with tertiary and quaternary stereocenters; efficient chemoenzymatic approaches to enantiopure α-methylated serine and isoserine derivatives

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2439-2444

  Wang, Mei Xiang ^a   Deng, Gang ^a   Wang, De Xian ^a   Zheng, Qi Yu ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CELLS; DERIVATIVES; ENZYMES; HYDRATION; NITROGEN COMPOUNDS; ORGANIC ACIDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

ENANTIOSELECTIVE SYNTHESIS; ISOSERINE DERIVATIVES; NITRILE BIOTRANSFORMATIONS; STEREOCENTERS;

BIOSYNTHESIS;

AMIDASE; AMIDE; CYANIDE; EPOXIDE; NITRILE HYDRATASE; PHENYLPROPIONIC ACID DERIVATIVE; PROPIONIC ACID;

ARTICLE; BIOTRANSFORMATION; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; RHODOCOCCUS; SUBSTITUTION REACTION;

AMIDES; BIOTRANSFORMATION; NITRILES; RHODOCOCCUS; SERINE; STEREOISOMERISM;

EID: 17044374655     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0482615     Document Type: Article

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33. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
34. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
35. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
36. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
37. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
38. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
39. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
40. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
41. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
42. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
43. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
44. For recent examples, see: (a) Wang, M.-X.; Lin, S.-J.; Liu, J.; Zheng, Q.-Y. Adv. Synth. Catal. 2004, 346, 439. (b) Wang, M.-X.; Lin, S.-J. J. Org. Chem. 2002, 67, 6542. (c) Wang, M.-X.; Zhao, S.-M. Tetrahedron Lett. 2002, 43, 6617. (d) Wang, M.-X.; Zhao, S.-M. Tetrahedron: Asymmetry 2002, 13, 1695. (e) Wang, M.-X.; Li, J.-J.; Ji, G.-J.; Li, J.-S. J. Mol. Catal. B: Enzymol. 2001, 14, 77. (f) Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925. (g) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron: Asymmetry 2001, 12, 3367. (h) Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123. (i) Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (j) DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (k) Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386. (l) Effenberger, F.; Osswald, S. Tetrahedron: Asymmetry 2001, 12, 279. (m) Hann, E. C.; Sigmund, A. E.; Fager, S. K.; Cooling, F. B.; Gavagan, J. E.; Ben-Bassat, A.; Chauhan, S.; Payne, M. S.; Hennessey, S. M.; DiCosimo, R. Adv. Synth. Catal. 2003, 345, 775. (n) Wu, Z.-L.; Li, Z.-Y. J. Mol. Catal. B: Enzymol. 2003, 22, 105, (o) Preiml, M.; Hillmayer, K.; Klempier, N. Tetrahedron Lett. 2003, 44, 5057. (p) Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fushuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
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