Highly enantioselective decarboxylative Mannich reaction of malonic acid half oxyesters with cyclic trifluoromethyl ketimines: Synthesis of β-amino esters and anti-HIV drug DPC 083

Chemistry - A European Journal

Volumn 19, Issue 47, 2013, Pages 15856-15860

  Yuan, Hai Na ^a   Li, Shen ^a   Nie, Jing ^a   Zheng, Yan ^a   Ma, Jun An ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

asymmetric catalysis; decarboxylative Mannich reaction; malonic acid half oxyesters; saccharide derived amino thioureas; amino esters

Indexed keywords

CARBOXYLIC ACIDS; ENANTIOSELECTIVITY; ESTERS;

AMINO ESTERS; ASYMMETRIC CATALYSIS; MALONIC ACID; MANNICH REACTIONS; SACCHARIDE-DERIVED AMINO-THIOUREAS;

ESTERIFICATION;

6 CHLORO 4 (2 CYCLOPROPYLVINYL) 3,4 DIHYDRO 4 TRIFLUOROMETHYL 2(1H) QUINAZOLINONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ESTER; IMINE; KETIMINE; MALONIC ACID; MALONIC ACID DERIVATIVE; NITRILE; QUINAZOLINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; DECARBOXYLATIVE MANNICH REACTION; MALONIC ACID HALF OXYESTERS; SACCHARIDE-DERIVED AMINO-THIOUREAS; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY; Β-AMINO ESTERS;

ASYMMETRIC CATALYSIS; DECARBOXYLATIVE MANNICH REACTION; MALONIC ACID HALF OXYESTERS; SACCHARIDE-DERIVED AMINO-THIOUREAS; Β-AMINO ESTERS;

ANTI-HIV AGENTS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ESTERS; IMINES; MALONATES; MOLECULAR CONFORMATION; NITRILES; QUINAZOLINES; STEREOISOMERISM;

EID: 84894452675     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303307     Document Type: Article

References (52)

1. M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035
2. J.-A. Ma, Angew. Chem. 2003, 115, 4426-4435
3. Angew. Chem. Int. Ed. 2003, 42, 4290-4299
4. E. Juaristi, V. A. Soloshonok, Enantioselective Synthesis of β-Amino Acids, Wiley, Hoboken, 2005
5. B. Weiner, W. Szymanski, D. B. Janssen, A. J. Minnaard, B. L. Feringa, Chem. Soc. Rev. 2010, 39, 1656-1691.
6. G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541-2569
7. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797-5815
8. J. M. M. Verkade, L. J. C. v. Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29-41
9. S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011, 111, 2626-2704.
10. C.-H. Tan, Y. Pan, Synthesis 2011, 2044-2053.
11. A. Ricci, D. Pettersen, L. Bernardi, F. Fini, M. Fochi, R. P. Herrera, V. Sgarzani, Adv. Synth. Catal. 2007, 349, 1037-1040.
12. J. Baudoux, P. Lefebvre, R. Legay, M. C. Lasne, J. Rouden, Green Chem. 2010, 12, 252-259.
13. Y. Pan, C. W. Kee, Z. Jiang, T. Ma, Y. Zhao, Y. Yang, H. Xue, C.-H. Tan, Chem. Eur. J. 2011, 17, 8363-8370.
14. N. Hara, S. Nakamura, M. Sano, R. Tamura, Y. Funahashi, N. Shibata, Chem. Eur. J. 2012, 18, 9276-9280.
15. C. Jiang, F. Zhong, Y. Lu, Beilstein J. Org. Chem. 2012, 8, 1279-1283
16. C.-F. Yang, C. Shen, J.-R. Wang, S.-K. Tian, Org. Lett. 2012, 14, 3092-3095
17. F. Zhong, C. Jiang, W. Yao, L.-W. Xu, Y. Lu, Tetrahedron Lett. 2013, 54, 4333-4336
18. H.-N. Yuan, S. Wang, J. Nie, W. Meng, Q. Yao, J.-A. Ma, Angew. Chem. 2013, 125, 3961-3965
19. Angew. Chem. Int. Ed. 2013, 52, 3869-3873.
20. K. Liu, H.-F. Cui, J. Nie, K.-Y. Dong, X.-J. Li, J.-A. Ma, Org. Lett. 2007, 9, 923-925
21. X.-J. Li, K. Liu, H. Ma, J. Nie, J.-A. Ma, Synlett 2008, 3242-3246
22. H. Ma, K. Liu, F.-G. Zhang, C.-L. Zhu, J. Nie, J.-A. Ma, J. Org. Chem. 2010, 75, 1402-1409
23. J. Nie, X.-J. Li, D.-H. Zheng, F.-G. Zhang, S. Cui, J.-A. Ma, J. Fluorine Chem. 2011, 132, 468-473
24. F. Li, L. Sun, Y. Teng, P. Yu, J. C.-G. Zhao, J.-A. Ma, Chem. Eur. J. 2012, 18, 14255-14260
25. W.-T. Meng, Y. Zheng, J. Nie, H.-Y. Xiong, J.-A. Ma, J. Org. Chem. 2012, 78, 559-567
26. J.-A. Ma, D. Cahard, J. Fluorine Chem. 2007, 128, 975-996
27. K. Uneyama, T. Katagiri, H. Amii, Acc. Chem. Res. 2008, 41, 817-829
28. N. Shibata, S. Mizuta, H. Kawai, Tetrahedron: Asymmetry 2008, 19, 2633-2644
29. Y. Zheng, J.-A. Ma, Adv. Synth. Catal. 2010, 352, 2745-2750
30. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475-4521
31. G. Valero, X. Companyó, R. Rios, Chem. Eur. J. 2011, 17, 2018-2037
32. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455-529
33. T. Besset, C. Schneider, D. Cahard, Angew. Chem. 2012, 124, 5134-5136
34. Angew. Chem. Int. Ed. 2012, 51, 5048-5050. For selected reviews on difluoromethyl chemistry see
35. J. Hu, W. Zhang, F. Wang, Chem. Commun. 2009, 7465-7478
36. C.-P. Zhang, Q.-Y. Chen, Y. Guo, J.-C. Xiao, Y.-C. Gu, Chem. Soc. Rev. 2012, 41, 4536-4559.
37. L. Fowden, Biochem. J. 1956, 64, 323-332
38. K. Isono, K. Asahi, S. Suzuki, J. Am. Chem. Soc. 1969, 91, 7490-7505
39. A. W. Bannon, M. W. Decker, M. W. Holladay, P. Curzon, D. Donnelly-Roberts, P. S. Puttfarcken, R. S. Bitner, A. Diaz, A. H. Dickenson, R. D. Porsolt, M. Williams, S. P. Arneric, Science 1998, 279, 77-80
40. A. Brandi, S. Cicchi, F. M. Cordero, Chem. Rev. 2008, 108, 3988-4035.
41. J. W. Corbett, S. S. Ko, J. D. Rodgers, L. A. Gearhart, N. A. Magnus, L. T. Bacheler, S. Diamond, S. Jeffrey, R. M. Klabe, B. C. Cordova, S. Garber, K. Logue, G. L. Trainor, P. S. Anderson, S. K. Erickson-Viitanen, J. Med. Chem. 2000, 43, 2019-2030.
42. B. Jiang, J. J. Dong, Y. G. Si, X. L. Zhao, Z. G. Huang, M. Xu, Adv. Synth. Catal. 2008, 350, 1360-1366
43. H. Xie, Y. Zhang, S. Zhang, X. Chen, W. Wang, Angew. Chem. 2011, 123, 11977-11980
44. Angew. Chem. Int. Ed. 2011, 50, 11773-11776
45. F.-G. Zhang, X.-Y. Zhu, S. Li, J. Nie, J.-A. Ma, Chem. Commun. 2012, 48, 11552-11554.
46. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296
47. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
48. Angew. Chem. Int. Ed. 2006, 45, 1520-1543
49. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
50. X. Yu, W. Wang, Chem. Asian 2008, 3, 516-532
51. Z. Zhang, P. R. Schreiner, Chem. Soc. Rev. 2009, 38, 1187-1198
52. S. Beckendorf, S. Asmus, O. G. Mancheño, ChemCatChem 2012, 4, 926-936.