Erratum: Correction to synthesis and application of enantioenriched functionalized α-tetrasubstituted α-Amino acids from biocatalytic desymmetrization of prochiral α-aminomalonamides (Journal of Organic Chemistry (2012) (77) 5584?5591. DOI: 10.1021/jo3007122));Synthesis and application of enantioenriched functionalized α-tetrasubstituted α-amino acids from biocatalytic desymmetrization of prochiral α-aminomalonamides

Journal of Organic Chemistry

Volumn 77, Issue 13, 2012, Pages 5584-5591

  Zhang, Li Bing ^a   Wang, De Xian ^a   Zhao, Liang ^b   Wang, Mei Xiang ^b  

^a PEKING UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

ALCOHOL DERIVATIVES; ALPHA-AMINO ACIDS; CHEMICAL TRANSFORMATIONS; DESYM-METRIZATION; PHOSPHATE BUFFERS; RHODOCOCCUS ERYTHROPOLIS; SYNTHETIC APPLICATION; WHOLE-CELL CATALYSTS;

AMINO ACIDS;

2 ALLYL 2 (DIMETHYLAMINO) MALONAMIDE; 2 ALLYL 2 (METHYLAMINO) MALONAMIDE; 2 ALLYL 2 AMINOMALONAMIDE; 2 AMINO 2 (BUT 2 EN 1 YL) MALONAMIDE; 2 AMINO 2 (BUT 2 YN 1 YL) MALONAMIDE; 2 AMINO 2 (BUT 3 EN 1 YL) MALONAMIDE; 2 AMINO 2 (PROP 2 YN 1 YL) MALONAMIDE; 2 AMINO 2 BENZYLMALONAMIDE; 2 AMINO 2 CARBAMOYL 3 PHENYLPROPANOIC ACID; 2 AMINO 2 CARBAMOYL 4 METHYLPENT 4 ENOIC ACID; 2 AMINO 2 CARBAMOYL 5 PHENYLPENT 4 ENOIC ACID; 2 AMINO 2 CARBAMOYLHEX 4 ENOIC ACID; 2 AMINO 2 CARBAMOYLHEX 4 YNOIC ACID; 2 AMINO 2 CARBAMOYLHEX 5 ENOIC ACID; 2 AMINO 2 CARBAMOYLPENT 4 ENOIC ACID; 2 AMINO 2 CARBAMOYLPENT 4 YNOIC ACID; 2 AMINO 2 CARBAMOYLPENTANOIC ACID; 2 AMINO 2 CARBAMOYLPROPANOIC ACID; 2 AMINO 2 CINNAMYLMALONAMIDE; 2 AMINO 2 METHYLMALONAMIDE; 2 AMINO 2 PROPYLMALONAMIDE; 2 AMINO 2(2 METHYLALLYL) MALONAMIDE; 2 CARBAMOYL 2 (METHYLAMINO) PENT 4 ENOIC ACID; ALPHA AMINOMALONAMIDE DERIVATIVE; AMINO ACID DERIVATIVE; AMINOALCOHOL; BENZYL (R) 2 (BENZYLAMINO) 2 CARBAMOYLPENT 4 ENOATE; DIAMINO ALCOHOL DERIVATIVE; SERINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOCATALYSIS; CHEMICAL STRUCTURE; DESYMMETRIZATION; ENANTIOSELECTIVITY; HYDROLYSIS; NONHUMAN; RHODOCOCCUS ERYTHROPOLIS; SYNTHESIS;

EID: 84863617582     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302041h     Document Type: Erratum

References (52)

1. Hudlicky, T. Chem. Rev. 2011, 111, 3995
2. Fessner, W.-D.; Turner, N. J.; Wang, M.-X. Adv. Synth. Catal. 2011, 353, 2189
3. García-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2011, 111, PR110
4. For a comprehensive summary, see: Hydrolysis and Formation of C-O Bonds in Enzyme Catalysis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, 1995; Vol. 1, pp 165-371.
5. Yokoyama, M.; Sugai, T.; Ohta, H. Tetrahedron: Asymmetry 1993, 4, 1081
6. Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fuhshuku, K.-i.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817
7. Wu, Z.-L.; Li, Z.-Y. Chem. Commun. 2003, 386
8. Wu, Z.-L.; Li, Z.-Y. J. Org. Chem. 2003, 68, 2479
9. Wu, Z.-L.; Li, Z.-Y. Tetrahedron: Asymmetry 2003, 14, 2133
10. Kakeya, H.; Sakai, N.; Sano, A.; Yokoyama, M.; Sugai, T.; Ohta, H. Chem. Lett. 1991, 1823
11. Crosby, J. A.; Parratt, J. S.; Turner, N. J. Tetrahedron: Asymmetry 1992, 3, 1547
12. Beard, T.; Cohen, M. A.; Parratt, J. S.; Turner, N. J.; Crosby, J.; Moilliet, J. Tetrahedron: Asymmetry 1993, 4, 1085
13. Wang, M.-X.; Liu, C.-S.; Li, J.-S.; Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549
14. 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
15. Meth-Cohn, O.; Wang, M.-X. J. Chem. Soc., Perkin Trans. 1 1997, 3197
16. Nagasawa, T.; Schimizu, H.; Yamada, H. Appl. Microbiol. Biotechnol. 1993, 40, 189
17. Wang, M.-X. Top. Catal. 2005, 35, 117
18. Wang, M.-X. Top. Organometal. Chem. 2011, 36, 105
19. Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci., Biotechnol., Biochem. 1997, 61, 1419
20. Martinkova, L.; Kren, V. Biocat. Biotrans. 2002, 20, 73
21. Blakey, A. J.; Colby, J.; Williams, E.; O'Reilly, C. FEMS Microbiol. Lett. 1995, 129, 57
22. Colby, J.; Snell, D.; Black, G. W. Monatsh. Chem. 2000, 131, 655
23. O'Mahony, R.; Doran, J.; Coffey, L.; Cahill, O. J.; Black, G. W.; O'Reilly, C. Antonie van Leeuwenhoek 2005, 87, 221
24. Wang, M.-X.; Lin, S.-J. Tetrahedron Lett. 2001, 42, 6925
25. Ma, D.-Y.; Wang, D.-X.; Pan, J.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2008, 73, 4087
26. Ma, D.-Y.; Zheng, Q.-Y.; Wang, D.-X.; Wang, M.-X. Org. Lett. 2006, 8, 3231
27. Gao, M.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. J. Org. Chem. 2006, 71, 9532 and ferences cited therein
28. Gao, M.; Wang, D.-X.; Zheng, Q.-Y.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2007, 72, 6060
29. Ma, D.-Y.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Tetrahedron: Asymmetry 2006, 17, 2366
30. Wang, M.-X.; Feng, G.-Q. Adv. Synth. Catal. 2003, 345, 695 and references cited therein.
31. Wang, M.-X.; Deng, G.; Wang, D.-X.; Zheng, Q.-Y. J. Org. Chem. 2005, 70, 2439 and references cited therein
32. Wang, J.-Y.; Wang, D.-X.; Pan, J.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2007, 72, 9391 and references cited therein.
33. Leng, D.-H.; Wang, D.-X.; Pan, J.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2009, 74, 6077
34. Leng, D.-H.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Org. Biomol. Chem. 2010, 8, 4736
35. Liu, J.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Chem. J. Chem 2006, 24, 1665
36. Zhang, L.-B.; Wang, D.-X.; Wang., M.-X. Tetrahedron 2011, 67, 5604
37. Liskamp, R. M. J.; Rijkers, D. T. S.; Kruijtzer, J. A. W.; Kemmink, J. ChemBioChem 2011, 12, 1626 and references cited therein.
38. Walensky, L. D.; Kung, A. L.; Escher, I.; Malia, T. J.; Barbuto, S.; Wright, R.; Wanger, G.; Verdine, G. L. Science 2004, 305, 1466
39. Kim, Y.-W.; Grossmann, T. N.; Verdine, G. L. Nat. Protoc. 2011, 6, 761
40. Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127 and references cited therein.
41. Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569 and references cited therein.
42. Vogt, H.; Bräse, S. Org. Biomol. Chem. 2007, 5, 406
43. Locquin, R.; Cerchez, V. Bull. Soc. Chim. Fr. 1931, 49, 42
44. O'Donnell, M. J. Acc. Chem. Res. 2004, 37, 506 and references cited therein.
45. Matsumoto, T.; Yoshida, D.; Tomita, H. Agric. Biol. Chem. 1981, 45, 2031
46. For a recent example, see: Chen, P.; Gao, M.; Wang, D.-X.; Zhao, L.; Wang, M.-X. J. Org. Chem. 2012, 77, 4063 and references cited therein.
47. Guo, X.-L.; Deng, G.; Xu, J.; Wang, M.-X. Enzyme Microb. Technol. 2006, 39, 1
48. Hawkins, M. J.; Greco, E.; de Garavilla, L.; Maryanoff, B. E. US Patent 20100048513 A1, 2010.
49. Uno, H.; Kasahara, K.-i.; Ono, N. Heterocycles 2000, 53, 1011
50. Shue, H.-J.; Chen, X.; Shih, N.-Y.; Blythin, D. J.; Paliwal, S.; Lin, L.; Gu, D.; Schwerdt, J. H.; Ahah, S.; Reichard, G. A.; Piwinski, J. J.; Duffy, R. A.; Lachowicz, J. E.; Coffin, V. L.; Liu, F.; Nomeir, A. A.; Morgan, C. A.; Varty, G. B. Bioorg. Med. Chem. Lett. 2005, 15, 3896
51. Tendler, S. J. B.; Threadgill, M. D.; Tisdale, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 2617
52. Mejer, S. Rocz. Chem. 1962, 36, 1115