Microbial whole cell-catalyzed desymmetrization of prochiral malonamides: Practical synthesis of enantioenriched functionalized carbamoylacetates and their application in the preparation of unusual α-amino acids

Tetrahedron

Volumn 67, Issue 31, 2011, Pages 5604-5609

  Zhang, Li Bin ^a   Wang, De Xian ^a   Wang, Mei Xiang ^a,b  

^a INSTITUTE OF CHEMISTRY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 (BUT 2 EN 1 YL) 2 METHYLMALONAMIDE; 2 ALLYL 2 (BUT 2 YN 1 YL)MALONAMIDE; 2 ALLYL 2 (PROP 2 YN 1 YL)MALONAMIDE; 2 ALLYL 2 METHYLMALONAMIDE; 2 BENZYL 2 (PROP 2 YN 1 YL)MALONAMIDE; 2 BENZYL 2 METHYLMALONAMIDE; 2 CINNAMYL 2 METHYLMALONAMIDE; 2 METHYL 2 (2 METHYLALLYL)MALONAMIDE; 2 METHYL 2 (PROP 2 YN 1 YL)MALONAMIDE; 2 METHYL 2 PROPYLMALONAMIDE; ACETIC ACID; ALPHA ALLYL ALPHA METHYLCARBAMOYLACETIC ACID; ALPHA AMINO ACID; AMIDE; CARBAMOYLACETATE; MALONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DESYMMETRIZATION; ENANTIOSELECTIVITY; NONHUMAN; PRIORITY JOURNAL; RHODOCOCCUS ERYTHROPOLIS; SYNTHESIS;

RHODOCOCCUS ERYTHROPOLIS;

EID: 79959735885     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.103     Document Type: Article

References (51)

1. For a review, see: K. Drauz, and H. Waldmann Hydrolysis and Formation of C-O Bonds Enzyme Catalysis in Organic Synthesis Vol. 1 1995 VCH Weinheim 165 371
2. For reviews on amidases in organic synthesis, see:
3. T. Sugai, T. Yamazaki, M. Yokoyama, and H. Ohta Biosci. Biotechnol. Biochem. 61 1997 1419
4. L. Martinkova, and V. Kren Biocat. Biotrans. 20 2002 73
5. Z.-L. Wu, and Z.-Y. Li J. Org. Chem. 68 2003 2479
6. For a related study involving amidase-catalyzed biotransformation, see M. Yokoyama, M. Kashiwagi, M. Iwasaki, K.-i. Fuhshuku, H. Ohta, and T. Sugai Tetrahedron: Asymmetry 15 2004 2817
7. A.J. Blakey, J. Colby, E. Williams, and C. O'Reilly FEMS Microbiol. Lett. 129 1995 57
8. R. O'Mahony, J. Doran, L. Coffey, O.J. Cahill, G.W. Black, and C. O'Reilly Antonie van Leeuwenhoek 87 2005 221
9. For reviews, see:
10. M.-X. Wang Top. Catal. 35 2005 117
11. M.-X. Wang Chimia 63 2009 331
12. For the synthesis of chiral carboxylic acids and amides bearing a functional group, see:
13. M.-X. Wang, and S.-M. Zhao Tetrahedron Lett. 43 2002 6617
14. M.-X. Wang, and S.-M. Zhao Tetrahedron: Asymmetry 13 2002 1695
15. D.-Y. Ma, D.-X. Wang, Q.-Y. Zheng, and M.-X. Wang Tetrahedron: Asymmetry 17 2006 2366
16. M. Gao, D.-X. Wang, Q.-Y. Zheng, and M.-X. Wang J. Org. Chem. 71 2006 9532
17. M. Gao, D.-X. Wang, Q.-Y. Zheng, Z.-T. Huang, and M.-X. Wang J. Org. Chem. 72 2007 6060
18. For the synthesis of chiral α- and β-amino and -hydroxy acids and amides, see:
19. M.-X. Wang, and S.-J. Lin J. Org. Chem. 67 2002 6542
20. M.-X. Wang, and Y. Wu Org. Biomol. Chem. 1 2003 535
21. M.-X. Wang, S.-J. Lin, J. Liu, and Q.-Y. Zheng Adv. Synth. Catal. 346 2004 439
22. M.-X. Wang, J. Liu, D.-X. Wang, and Q.-Y. Zheng Tetrahedron: Asymmetry 16 2005 2409
23. D.-Y. Ma, Q.-Y. Zheng, D.-X. Wang, and M.-X. Wang Org. Lett. 8 2006 3231
24. D.-Y. Ma, D.-X. Wang, J. Pan, Z.-T. Huang, and M.-X. Wang Tetrahedron: Asymmetry 19 2008 322
25. D.-Y. Ma, D.-X. Wang, J. Pan, Z.-T. Huang, and M.-X. Wang J. Org. Chem. 73 2008 4087
26. J. Liu, D.-X. Wang, Q.-Y. Zheng, and M.-X. Wang Chem. J. Chem. 24 2006 1665
27. For the synthesis of chiral cyclopropanecarboxylic acids and amides, see:
28. M.-X. Wang, and G.-Q. Feng Tetrahedron Lett. 41 2000 6501
29. M.-X. Wang, and G.-Q. Feng J. Mol. Catal. B: Enzym. 18 2002 267
30. M.-X. Wang, and G.-Q. Feng New J. Chem. 26 2002 1575
31. M.-X. Wang, and G.-Q. Feng Adv. Synth. Catal. 345 2003 695
32. M.-X. Wang, and G.-Q. Feng J. Org. Chem. 68 2003 621
33. M.-X. Wang, G.-Q. Feng, and Q.-Y. Zheng Tetrahedron: Asymmetry 15 2004 347
34. For the synthesis of chiral oxiranecarboxamides, see:
35. M.-X. Wang, S.-J. Lin, C.-S. Liu, Q.-Y. Zheng, and J.-S. Li J. Org. Chem. 68 2003 4570
36. M.-X. Wang, G. Deng, D.-X. Wang, and Q.-Y. Zheng J. Org. Chem. 70 2005 2439
37. For the synthesis of chiral aziridinecarboxylic acids and amides, see:
38. J.-Y. Wang, D.-X. Wang, Q.-Y. Zheng, Z.-T. Huang, and M.-X. Wang J. Org. Chem. 72 2007 2040
39. J.-Y. Wang, D.-X. Wang, J. Pan, Z.-T. Huang, and M.-X. Wang J. Org. Chem. 72 2007 9391
40. For the synthesis of chiral azetidine- and azetidinone-carboxylic acids and amides, see:
41. D.-H. Leng, D.-X. Wang, J. Pan, and Z.-T. Huang J. Org. Chem. 74 2009 6077
42. D.-H. Leng, D.-X. Wang, and Z.-T. Huang Org. Biomol. Chem. 8 2010 4736
43. X.-L. Guo, G. Deng, J. Xu, and M.-X. Wang Enzyme Microb. Technol. 39 2006 1
44. W. Qiu, V.A. Soloshonok, C.-Z. Cai, X.-J. Tang, and V.J. Hruby Tetrahedron 56 2000 2577
45. N.B. Yuri, I.B. Vladimir, I.C. Nina, A.K. Konstantin, V.V. Sergei, S.G. Natalia, and M.B. Vasili J. Chem. Soc., Perkin Trans. 1 1988 305
46. E.S. Christian, P. Julia, and L.V. Gregory J. Am. Chem. Soc. 122 2000 5891
47. S. Aurash, S.K. James, A.L. Elizabeth, A.S. Bruce, M.H. James, W.H. Harriet, K.S. Tomi, H. Christine, and M.D. Annette J. Med. Chem. 38 1995 2893
48. Y.Q. Long, T. Xue, Y.L. Song, Z.L. Liu, S.X. Huang, and Q. Yu J. Med. Chem. 51 2008 6371
49. H. Meyer Ber. 39 1906 198
50. M.-X. Wang, G. Lu, G.-J. Ji, Z.-T. Huang, M. Meth-Cohn, and J. Colby Tetrahedron: Asymmetry 11 2000 1123
51. M. Lee, Y.-H. Jin, H. Dong, and B. Kim Med. Chem. 7 1999 1755