Biotransformations of racemic 2,3-allenenitriles in biphasic systems: Synthesis and transformations of enantioenriched axially chiral 2,3-allenoic acids and their derivatives

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3103-3110

  Ao, Yu Fei ^a   Wang, De Xian ^a   Zhao, Liang ^b   Wang, Mei Xiang ^b  

^a INSTITUTE OF CHEMISTRY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; CYANIDES; HYDROLYSIS;

AMIDE HYDROLYSIS; AXIAL CHIRALITY; BIPHASIC SYSTEMS; ENANTIOSELECTIVE; FUNCTIONALIZED; HETEROCYCLIC COMPOUND; RHODOCOCCUS ERYTHROPOLIS; WHOLE CELL;

CATALYSIS;

ALLENE DERIVATIVE; HEXANE; NITRILE HYDRATASE; ALKADIENE; HETEROCYCLIC COMPOUND; HYDROLYASE; N-HEXANE; NITRILE; PROPADIENE;

ARTICLE; BIOCATALYSIS; BIOTRANSFORMATION; CHIRALITY; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; DIMERIZATION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HYDRATION; HYDROLYSIS; NONHUMAN; RHODOCOCCUS ERYTHROPOLIS; STEREOSPECIFICITY; SYNTHESIS; WHOLE CELL; CATALYSIS; CHEMISTRY; ENZYMOLOGY; METABOLISM; RHODOCOCCUS; STEREOISOMERISM;

ALKADIENES; BIOTRANSFORMATION; CATALYSIS; HETEROCYCLIC COMPOUNDS; HEXANES; HYDRO-LYASES; HYDROLYSIS; NITRILES; RHODOCOCCUS; STEREOISOMERISM;

EID: 84898070284     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500228z     Document Type: Article

References (78)

1. Ma, S.-M. Chem. Rev. 2005, 105, 2829
2. Ma, S.-M. Aldrichimica Acta 2007, 40, 91
3. Brasholz, M.; Reissig, H.-U.; Zimmer, R. Acc. Chem. Res. 2009, 42, 45
4. Ma, S.-M. Acc. Chem. Res. 2009, 42, 1679
5. Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954
6. Yu, S.-C.; Ma, S.-M. Angew. Chem., Int. Ed. 2012, 51, 3074
7. Zeng, R.; Fu, C.; Ma, S.-M. J. Am. Chem. Soc. 2012, 134, 9597
8. Butler, K. L.; Tragni, M.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2012, 51, 5175
9. Adams, C. S.; Boralsky, L. A.; Guzei, I. A.; Schomaker, J. M. J. Am. Chem. Soc. 2012, 134, 10807
10. Cai, F.; Pu, X.; Qi, X.; Lynch, V.; Radha, A.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 18066
11. Ogasawara, M. Tetrahedron: Asymmetry 2009, 20, 259
12. Yu, S.; Ma, S.-M. Chem. Commun. 2011, 47, 5384
13. Wan, B.-Q.; Ma, S.-M. Angew. Chem., Int. Ed. 2013, 52, 441
14. Ye, J.; Lü, R.; Fan, W.; Ma, S.-M. Tetrahedron 2013, 69, 8959
15. Ye, J.; Fan, W.; Ma, S.-M. Chem.-Eur. J. 2013, 19, 716
16. Ogasawara, M.; Ge, Y.; Okada, A.; Takahashi, T. Eur. J. Org. Chem. 2012, 1656
17. Ye, J.; Li, S.; Chen, B.; Fan, W.; Kuang, J.; Liu, J.; Liu, Y.; Miao, B.; Wan, B.; Wang, Y.; Xie, X.; Yu, Q.; Yuan, W.; Ma, S.-M. Org. Lett. 2012, 14, 1346
18. Li, H.; Müller, D.; Guénée, L.; Alexakis, A. Org. Lett. 2012, 14, 5880
19. Zhang, W.; Zheng, S.; Liu, Z.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664
20. Nishimura, T.; Makino, H.; Nagaosa, M.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 12865
21. Lo, V. K.-Y.; Zhou, C.-Y.; Wong, M.-K.; Che, C.-M. Chem. Commun. 2010, 46, 213
22. For a review, see: Cowen, B.-J.; Miller, S.-J. Chem. Soc. Rev. 2009, 38, 3102
23. For an overview, see: Wang, Y.; Ma, S.-M. Adv. Synth. Catal. 2013, 355, 741 and references cited therein
24. Molander, G. A.; Sommers, E. M.; Baker, S. R. J. Org. Chem. 2006, 71, 1563
25. Kobayashi, K.; Naka, H.; Wheatley, A. E. H.; Kondo, Y. Org. Lett. 2008, 10, 3375
26. Pinho e Melo, T. M. V. D.; Cardoso, A. L.; Rocha Gonsalves, A. M. d?A.; Pessoa, J. C.; Paixão, J. A.; Beja, A. M. Eur. J. Org. Chem. 2004, 4830
27. Yamazaki, J.; Watanabe, T.; Tanaka, K. Tetrahedron: Asymmetry 2001, 12, 669
28. Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.-i.; Uemura, S. J. Org. Chem. 1995, 60, 4114
29. Yu, J.; Chen, W.-J.; Gong, L.-Z. Org. Lett. 2010, 12, 4050
30. Ramaswamy, S.; Hui, R. A. H.; Jones, B. J. Chem. Soc., Chem. Commum. 1986, 1545
31. Pietzsch, M.; Vielhauer, O.; Pamperin, D.; Ohse, B.; Hopf, H. J. Mol. Catal. B: Enzym. 1999, 6, 51
32. Carballeira, J. D.; Krumlinde, P.; Bocola, M.; Vogel, A.; Reetz, M. T.; Bäckvall, J.-E. Chem. Commun. 2007, 1913
33. Li, C.-Y.; Wang, X.-B.; Sun, X.-L.; Tang, Y.; Zheng, J.-C.; Xu, Z.-H.; Zhou, Y.-G.; Dai, L.-X. J. Am. Chem. Soc. 2007, 129, 1494
34. Liu, H.; Leow, D.; Huang, K.-W.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 7212
35. Inokuma, T.; Furukawa, M.; Uno, T.; Suzuki, Y.; Yoshida, K.; Yano, Y.; Matsuzaki, K.; Takemoto, Y. Chem.-Eur. J. 2011, 17, 10470
36. Wang, Y.-L.; Zhang, W.-L.; Ma, S.-M. J. Am. Chem. Soc. 2013, 135, 11517
37. Qian, H.; Yu, X.; Zhang, J.; Sun, J. J. Am. Chem. Soc. 2013, 135, 18020
38. Crouch, I. T.; Neff, R. K.; Frantz, D. E. J. Am. Chem. Soc. 2013, 135, 4970
39. Hashimoto, T.; Sakata, K.; Tamakuni, F.; Dutton, M. J.; Maruoka, K. Nat. Chem. 2013, 5, 240
40. For an overview, see: Wang, M.-X. Top. Catal. 2005, 35, 117
41. Ramteke, P. W.; Maurice, N. G.; Joseph, B.; Wadher, B. J. Biotechnol. Appl. Biochem. 2013, 60, 459
42. Prasad, S.; Bhalla, T. C. Biotechnol. Adv. 2010, 28, 725
43. Velankar, H.; Clarke, K. G.; du Preez, R.; Cowan, D. A.; Burton, S. G. Trends Biotechnol. 2010, 28, 561
44. DAntona, N.; Morrone, R. Biocatalysis: Green Transformations of Nitrile Function. In Green Chemistry for Environmental Sustainability; Sharma, S. K.; Mudhoo, A., Eds.; CRC Press: Boca Raton, FL, 2010.
45. Busto, E.; Gotor-Fernández, V.; Gotor, V. Chem. Rev. 2011, 111, 3998
46. Ordóñez, M.; Cativiela, C. Tetrahedron: Asymmetry 2007, 18, 3
47. Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569
48. Gröger, H. Enzyme-Catalyzed Asymmetric Synthesis. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2010.
49. Blakey, A. J.; Colby, J.; Williams, E.; OReilly, C. FEMS Microbiol. Lett. 1995, 129, 57
50. OMahony, R.; Doran, J.; Coffey, L.; Cahill, O. J.; Black, G. W.; OReilly, C. Antonie van Leeuwenhoek 2005, 87, 221
51. Wang, M.-X.; Lu, G.; Ji, G.-J.; Huang, Z.-T.; Meth-Cohn, O.; Colby, J. Tetrahedron: Asymmetry 2000, 11, 1123
52. Wang, M.-X. Top. Organomet. Chem. 2011, 36, 105
53. Wang, M.-X. Chimia 2009, 63, 331
54. Zhang, L.-B.; Wang, D.-X.; Zhao, L.; Wang, M.-X. J. Org. Chem. 2012, 77, 5584
55. Zhang, L.-B.; Wang, D.-X.; Wang, M.-X. Tetrahedron 2011, 67, 5604
56. Chen, P.; Gao, M.; Wang, D.-X.; Zhao, L.; Wang, M.-X. Chem. Commun. 2012, 48, 3482
57. Chen, P.; Gao, M.; Wang, D.-X.; Zhao, L.; Wang, M.-X. J. Org. Chem. 2012, 77, 4063
58. Beard, T.; Cohen, M. A.; Parratt, J. S.; Turner, N. J.; Crosby, J.; Miolliet, J. Tetrahedron: Asymmetry 1993, 4, 1085
59. Lang, R. W.; Hansen, H. J. Helv. Chim. Acta 1980, 63, 438
60. Cumper, C. W. N.; Fomum, Z. T.; Greaves, P. M.; Landor, S. R. J. Chem. Soc., Perkin Trans. II 1973, 885
61. Greaves, P. M.; Landor, P. D.; Landor, S. R.; Odyek, O. Tetrahedron Lett. 1973, 3, 209
62. Isken, S.; de Bont, J. A. M. Extremophiles 1998, 2, 229
63. Heipieper, H. J.; Neumann, G.; Cornelissen, S.; Meinhardt, F. Appl. Microbiol. Biotechnol. 2007, 74, 961
64. Shingu, K.; Hagishita, S.; Nakagawa, M. Tetrahedron Lett. 1967, 4371
65. Song, L.; Wang, M.; Shi, J.; Xue, Z.; Wang, M.-X.; Qian, S. Biochem. Biophys. Res. Commun. 2007, 362, 319
66. Gao, M.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. J. Org. Chem. 2006, 71, 9532
67. Gao, M.; Wang, D.-X.; Zheng, Q.-Y.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2007, 72, 6060
68. Ishar, M. P. S.; Wali, A.; Gandhi, R. P. J. Chem. Soc., Perkin Trans. 1 1990, 2185
69. Yu, J.; He, L.; Chen, X.-H.; Song, J.; Chen, W.-J.; Gong, L.-Z. Org. Lett. 2009, 11, 4946
70. Ma, S.-M.; Xie, H. Tetrahedron 2005, 61, 251
71. Greaves, P. M.; Landor, S. R.; Laws, D. R. J. J. Chem. Soc. C 1968, 291
72. Kurtz, P.; Gold, H.; Disselnkotter, H. Liebigs Ann. Chem. 1959, 1
73. Shi, J.; Zhang, M.; Fu, Y.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 12681
74. Jones, E. R. H.; Whitham, G. H.; Whiting, M. C. J. Chem. Soc. 1957, 4628
75. Mansfield, G. H.; Whiting, M. C. J. Chem. Soc. 1956, 4761
76. Wang, B.; Li, J.-Q.; Cheng, Y. Tetrahedron Lett. 2008, 49, 485
77. Musierowicz, S.; Wroblewski, A.; Krawczyk, H. Tetrahedron Lett. 1975, 437
78. Yamazaki, J.; Watanabe, T.; Tanaka, K. Tetrahedron: Asymmetry 2001, 12, 669