β-amino acid catalyzed asymmetric michael additions: Design of organocatalysts with catalytic acid/base dyad inspired by serine proteases

Journal of Organic Chemistry

Volumn 76, Issue 18, 2011, Pages 7399-7405

  Yang, Hui ^a   Wong, Ming Wah ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; BIO-INSPIRED; CATALYTIC ACIDS; DFT CALCULATION; DIASTEREOSELECTIVITIES; ENAMINE INTERMEDIATES; ENZYME CATALYSIS; HYDROGEN BONDING NETWORK; MICHAEL ADDITIONS; NITROALKENES; ORGANOCATALYSTS; SERINE PROTEASE; TRANSITION STATE;

ALDEHYDES; CATALYSIS; CATALYSTS; ENANTIOSELECTIVITY; HYDROGEN BONDS; STEREOSELECTIVITY;

AMINO ACIDS;

ACID; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; BASE; BETA AMINO ACID; CARBOXYL GROUP; IMIDAZOLE; NITRO DERIVATIVE; SERINE PROTEINASE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; ENANTIOSELECTIVITY; GEOMETRY; HYDROGEN BOND; MICHAEL ADDITION; STEREOCHEMISTRY;

ACIDS; ALKALIES; AMINO ACIDS; CATALYSIS; SERINE PROTEASES; STEREOISOMERISM;

EID: 80052756991     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2011413     Document Type: Article

References (47)

1. MacMillan, D. W. C. Nature 2008, 455, 304-308
2. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-517
3. Berkessel, A.; Groeger, G. In Asymmetric Organocatalysis: from Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Weinheim, 2005.
4. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
5. List, B. Tetrahedron 2002, 58, 5573-5590
6. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396
7. Calderon, F.; Doyaguez, E. G.; Cheong, P. H.; Fernandez-Mayoralas, A.; Houk, K. N. J. Org. Chem. 2008, 73, 7916-7920
8. Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 12911-12912
9. Rankin, K. N.; Gauld, J. W.; Boyd, R. J. J. Phys. Chem. A 2002, 106, 5155-5159
10. Garrett, R. H.; Grisham, C. M. Biochemistry, 4 th ed.; Brooks/Cole, Cengage Learning: Boston, 2010; pp 434-439.
11. Kasserra, H. P.; Laidler, K. J. Can. J. Chem. 1969, 47, 4031-4039
12. Kona, J. Org. Biomol. Chem. 2008, 6, 359-365
13. Menard, R.; Khouri, H. E.; Plouffe, C.; Laflamme, P.; Dupras, R.; Vernet, T.; Tessier, D. C.; Thomas, D. Y.; Storer, A. C. Biochemistry 1991, 30, 5531-5538
14. Khersonsky, O.; Tawfik, D. S. J. Biol. Chem. 2006, 281, 7649-7656
15. Schultz, L. W.; Quirk, D. J.; Raines, R. T. Biochemistry 1998, 37, 8886-8898
16. Botos, I.; Melnikov, E. E.; Cherry, S.; Tropea, J. E.; Khalatova, A. G.; Rasulova, F.; Dauter, Z.; Maurizi, M. R.; Rotanova, T. V.; Wlodawer, A.; Gustchina, A. J. Biol. Chem. 2004, 279, 8140-8148
17. Raber, M. L.; Arnett, S. O.; Townsend, C. A. Biochemistry 2009, 48, 4959-4971
18. Houk, K. N.; Cheong, P. H. Nature 2008, 455, 309-313
19. Mitsumori, S.; Zhang, H.; Cheong, P. H.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2006, 128, 1040-1041
20. Fleming, E. M.; Quigley, C.; Rozas, I.; Connon, S. J. J. Org. Chem. 2008, 73, 948-956
21. Shinisha, C. B.; Sunoj, R. B. Org. Biomol. Chem. 2007, 5, 1287-129
22. Armstrong, A.; Bhonoah, Y.; White, A. J. P. J. Org. Chem. 2009, 74, 5041-5048
23. Pihko, P. M.; Majander, I.; Erkila, A. Top. Curr. Chem. 2009, 291, 29-74
24. Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157
25. Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17
26. List, B.; Hoang, L.; Martin, H. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5839-5842
27. Shinisha, C. B.; Sunoj, R. B. Angew. Chem., Int. Ed. 2010, 49, 6373-6377
28. Calderon, F.; Doyaguez, E. G.; Cheong, P. H.; Fernandez-Mayoralas, A.; Houk, K. N. J. Org. Chem. 2008, 73, 7916-7920
29. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
30. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-355
31. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221
32. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926
33. Frisch, M. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
34. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701-1716
35. Vicario, J. L.; Badía, D.; Carrillo, L. Synthesis 2007, 2065-2092
36. Sulzer-Mossé, S.; Alexakis, A. Chem. Commun. 2007, 3123-3135
37. Notz, W.; Tanaka, F.; Barbas, C. F., III Acc. Chem. Res. 2004, 37, 580-591
38. Uehara, H.; Barbas, C. F., III Angew. Chem., Int. Ed. 2009, 48, 9848-9852
39. Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737-3740
40. Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876-7880
41. Andrey, O.; Alexakis, A.; Tomassini, A.; Bernardinelli, G. Adv. Synth. Catal. 2004, 346, 1147-1168
42. Palomo, C; Vera, S.; Mielgo, A.; Gomez-Bengoa, E. Angew. Chem., Int. Ed. 2006, 45, 5984-5987
43. Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L.; Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227-408.
44. Seebach, D. Angew. Chem., Int. Ed. 2011, 50, 96-101
45. Xiao, K.; Luo, J.; Ye, K.; Wang, Y.; Huang, P. Angew. Chem., Int. Ed. 2010, 49, 3037-304
46. Davies., S. G.; Russell., A. J.; Sheppard, R. L.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem. 2007, 5, 3190-3200
47. Limbach, M. Tetrahedron Lett. 2006, 47, 3843-3847