Organocatalytic asymmetric mannich reactions of 5H-oxazol-4-ones: Highly enantio- and diastereoselective synthesis of chiral α-alkylisoserine derivatives

Advanced Synthesis and Catalysis

Volumn 355, Issue 8, 2013, Pages 1505-1511

  Han, Zhiqiang ^a   Yang, Wenguo ^a   Tan, Choon Hong ^a,b   Jiang, Zhiyong ^a,b  

^a HENAN UNIVERSITY   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

alkyl hydroxy amino acids; 5H oxazol 4 ones; asymmetric catalysis; Mannich reaction; N triisopropylbenzenesulfonylimines

Indexed keywords

EID: 84878216298     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300135     Document Type: Article

References (50)

1. G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 25, 117
2. D. Seebach, J. L. Mattews, Chem. Commun. 1997, 2015
3. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173
4. Enantioselective Synthesis of β-Amino Acids, (Eds.:, E. Juaristi, V. A. Soloshonok,), John Wiley & Sons, Inc., Hoboken, New Jersey, 2005. For selected examples, see
5. K. Iizuka, T. Kamijo, T. Kubota, K. Akahane, H. Umeyama, Y. Kiso, J. Med. Chem. 1988, 31, 701
6. F. Fringuelli, F. Pizzo, M. Rucci, L. Vaccaro, J. Org. Chem. 2003, 68, 7041
7. S. Weik, T. Luksch, A. Evers, J. Böttcher, C. A. Sotriffer, A. Hasilik, H.-G. Löffler, G. Klebe, J. Rademaan, ChemMedChem 2006, 1, 445.
8. K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38
9. Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references cited therein.
10. I. Ojima, C. M. Sun, M. Zucco, Y. H. Park, O. Duclo, S. Kuduk, Tetrahedron Lett. 1993, 34, 4149
11. S. H. Chen, V. Farina, Paclitaxel (Taxol)-Chemistry and Structure-Activity Relationships, in: The Chemistry and Pharmacology of Taxol and its Derivatives, (Ed.:, V. Farina,), Elsevier, Amsterdam, 1995, p. 165
12. J.-H. Denis, A. Fkyerat, Y. Gimbert, C. Coutterez, P. Mantellier, S. Jost, A. E. Greene, J. Chem. Soc. Perkin Trans. 1 1995, 1811
13. J. Kant, W. S. Schwartz, C. Fairchild, Q. Gao, S. Huang, B. H. Long, J. F. Kadow, D. R. Langley, V. Farina, D. Vyas, Tetrahedron Lett. 1996, 37, 6495
14. I. Ojima, T. Wang, F. Delaloge, Tetrahedron Lett. 1998, 39, 3663
15. G. Cardillo, L. Gentilucci, A. Tolomelli, C. Tomasini, J. Org. Chem. 1998, 63, 2351
16. A. M. Nocioni, C. Papa, C. Tomasini, Tetrahedron Lett. 1999, 40, 8453
17. G. Cardillo, A. Tolomelli, C. Tomasini, Eur. J. Org. Chem. 1999, 155
18. Y. Takeda, T. Yoshino, K. Uoto, J. Chiba, T. Ishiyama, M. Iwahana, T. Jimbo, N. Tanaka, H. Terasawa, T. Soga, Bioorg. Med. Chem. Lett. 2003, 13, 185.
19. E. Turos, T. E. Long, B. Heldreth, J. M. Leslie, G. S. K. Reddy, Y. Wang, C. Coates, M. Konaklieva, S. Dickey, D. V. Lim, E. Alonso, J. Gonzalez, Bioorg. Med. Chem. Lett. 2006, 16, 2084.
20. M.-X. Wang, G. Deng, D.-X. Wang, Q.-Y. Zheng, J. Org. Chem. 2005, 70, 2439
21. N. C. Giampietro, J. P. Wolf, Angew. Chem. 2010, 122, 2984
22. Angew. Chem. Int. Ed. 2010, 49, 2922
23. D. Zhao, L. Wang, D. Yang, Y. Zhang, R. Wang, Angew. Chem. 2012, 124, 7641
24. Angew. Chem. Int. Ed. 2012, 51, 7523.
25. J. Luo, H. Wang, X. Han, L.-W. Xu, J. Kwiatkowski, K.-W. Huang, Y. Lu, Angew. Chem. 2011, 123, 1901
26. Angew. Chem. Int. Ed. 2011, 50, 1861
27. C. Liu, X. Dou, Y. Lu, Org. Lett. 2011, 13, 5248. For our recent examples, see
28. Y. Yang, F. Moinodeen, W. Chin, T. Ma, Z. Jiang, C.-H. Tan, Org. Lett. 2012, 14, 4762
29. W. Zhang, D. Tan, R. Lee, G. Tong, W. Chen, B. Qi, K.-W. Huang, C.-H. Tan, Z. Jiang, Angew. Chem. 2012, 124, 10216
30. Angew. Chem. Int. Ed. 2012, 51, 10069.
31. B. M. Trost, K. Dogra, M. Franzini, J. Am. Chem. Soc. 2004, 126, 1944.
32. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc. 2010, 132, 6286
33. T. Misaki, K. Kawano, T. Sugimura, J. Am. Chem. Soc. 2011, 133, 5695.
34. H. Huang, K. Zhu, W. Wu, Z. Jin, J. Ye, Chem. Commun. 2012, 48, 461.
35. B. M. Trost, K. Hirano, Angew. Chem. 2012, 124, 6586
36. Angew. Chem. Int. Ed. 2012, 51, 6480.
37. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289
38. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
39. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550
40. Angew. Chem. Int. Ed. 2006, 45, 1520
41. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
42. S. J. Connon, Chem. Commun. 2008, 2499
43. X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516. For our recent example using Cinchona alkaloid thiourea bifunctional catalyst, see
44. F. Zhao, W. Zhang, Y. Yang, Y. Pan, W. Chen, H. Liu, L. Yan, C.-H. Tan, Z. Jiang, Adv. Synth. Catal. 2011, 353, 2624.
45. J. R. Reid, R. F. Dufresne, J. J. Chapman, Organic Syntheses 1998, 9, 281.
46. T. Hayashi, M. Kawai, N. Tokunaga, Angew. Chem. 2004, 116, 6251
47. Angew. Chem. Int. Ed. 2004, 43, 6125.
48. T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2008, 350, 399
49. Y. Zhang, Y.-K. Liu, T.-R. Kang, Z.-K. Hu, Y.-C. Chen, J. Am. Chem. Soc. 2008, 130, 2456.
50. 2 at room temperature within 12 hours, 84 % yield of 11b was obtained. CCDC 917270 (11b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.