Decarboxylative arylation of α-Amino acids via photoredox catalysis: A one-step conversion of biomass to drug pharmacophore

Journal of the American Chemical Society

Volumn 136, Issue 14, 2014, Pages 5257-5260

  Zuo, Zhiwei ^a   Macmillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS;

ACID PRECURSORS; ARYLATIONS; BENZYLIC AMINES; PHARMACOPHORES; PHOTOREDOX CATALYSIS;

AMINO ACIDS;

ALPHA AMINO ACID; AMINE; POLYCYCLIC AROMATIC HYDROCARBON; AMINO ACID;

ARTICLE; ARYLATION; BIOMASS CONVERSION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DECARBOXYLATION; LIGHT; OXIDATION REDUCTION REACTION; PHARMACOPHORE; PHOTOCATALYSIS; CATALYSIS; CHEMISTRY; PHOTOCHEMISTRY;

AMINO ACIDS; CATALYSIS; DECARBOXYLATION; LIGHT; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES;

EID: 84898006720     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501621q     Document Type: Article

References (42)

1. Lehninger, A. L.; Nelson, D. L.; Cox, M. M. Principles of Biochemistry; Worth Publishers: New York, 1993.
2. Walsh, C. Enzymatic Reaction Mechanisms; W. H. Freeman and Co.: New York, 1979.
3. van Poelje, P. D.; Snell, E. E. Annu. Rev. Biochem. 1990, 59, 29
4. Vijh, A. K.; Conway, B. E. Chem. Rev. 1967, 67, 623
5. Johnson, R. G.; Ingham, R. K. Chem. Rev. 1956, 56, 219
6. Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279
7. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901
8. Kolbe, H. Liebigs Ann. Chem. 1849, 69, 257
9. Hunsdiecker, H.; Hunsdiecker, C. Chem. Ber. 1942, 75B, 291
10. Barton, D. H. R.; Serebryakov, E. P. Proc. Chem. Soc. 1962, 309
11. For examples of the use of biomass conversion to non-fuel, high-value chemical products see: Scott, E.; Peter, F.; Sanders, J. Appl. Microbiol. Biotechnol. 2007, 75, 751
12. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
13. Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
14. Gooßen, L. J.; Rodriguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100
15. Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653
16. Dzik, W. I.; Lange, P. P.; Gooßen, L. J. Chem. Sci. 2012, 3, 2671
17. Lawrence, S. A. Amines: Synthesis, Properties, and Applications; Cambridge University Press: Cambridge, 2004.
18. Lewis, J. R. Nat. Prod. Rep. 2001, 95
19. Lin, N.-H.; Carrera, G. M.; Anderson, D. J. J. Med. Chem. 1994, 37, 3542
20. Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C. J. Am. Chem. Soc. 2006, 128, 3538
21. Coldham, I.; Leonori, D. Org. Lett. 2008, 10, 3923
22. Beng, T. K.; Gawley, R. E. Org. Lett. 2011, 13, 394
23. Seel, S.; Thaler, T.; Takatsu, K.; Zhang, C.; Zipse, H.; Straub, B. F.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2011, 133, 4774
24. Nicewicz, D.; MacMillan, D. W. C. Science 2008, 322, 77
25. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
26. Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600
27. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
28. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617
29. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102
30. Teply, F. Collect. Czech. Chem. Commun. 2011, 76, 859
31. Flamigni, L.; Barbieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. Top. Curr. Chem. 2007, 281, 143
32. Dixon, I. M.; Collin, J.; Sauvage, J.; Flamigni, L.; Encinas, S.; Barigelletti, F. Chem. Soc. Rev. 2000, 29, 385
33. Mori, Y.; Sakaguchi, W.; Hayashi, H. J. Phys. Chem. A 2000, 104, 4896
34. Studer, A. Chem.-Eur. J. 2001, 7, 1159
35. Andrieux, C. P.; Gonzalez, F.; Saveant, J. J. Electroanal. Chem. 2001, 498, 171
36. Galicia, M.; Gonzalez, F. J. J. Electrochem. Soc. 2002, 149, D46
37. Dedeian, K.; Djurovich, P. I.; Garces, F. O.; Carlson, G.; Watts, R. J. Inorg. Chem. 1991, 30, 1685
38. Tian, N.; Lenkeit, D.; Pelz, S.; Fischer, L. H.; Escudero, D.; Schiewek, R.; Klink, D.; Schmitz, O. J.; Gonzalez, L.; Schaferling, M.; Holder, E. Eur. J. Inorg. Chem. 2010, 4875
39. Balzani, V.; Bolletta, F.; Gandolfi, M. T.; Maestri, M. Top. Curr. Chem. 1978, 75, 1
40. Lowry, M. S.; Goldsmith, J. I.; Slinker, J. D.; Rohl, R.; Pascal, R. A.; Malliaras, G.; Bernhard, S. Chem. Mater. 2005, 17, 5712
41. Damm, W.; Giese, B.; Hartung, J.; Hasskerl, T.; Houk, K. N.; Hueter, O.; Zipse, H. J. Am. Chem. Soc. 1992, 114, 4067
42. Arnaud, R.; Postlethwaite, H.; Barone, V. J. Phys. Chem. 1994, 98, 5913