Visible-light photoredox synthesis of unnatural chiral α-amino acids

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Jiang, Min ^a   Jin, Yunhe ^a   Yang, Haijun ^a   Fu, Hua ^a  

^a Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID;

LIGHT; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; PROCEDURES; SYNTHESIS; TEMPERATURE;

AMINO ACIDS; CHEMISTRY, ORGANIC; LIGHT; OXIDATION-REDUCTION; TEMPERATURE;

EID: 84969245665     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep26161     Document Type: Article

References (31)

1. Hughes A. B. Amino Acids, Peptides and Proteins in Organic Chemistry (Wiley-VCH, Weinheim, 2009
2. Coppola G. M., & Schuster H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids (Wiley: New York, 1987
3. Najera C., & Sansano J. M. Catalytic asymmetric synthesis of α -amino acids. Chem. Rev. 107, 4584-4671 (2007
4. Blaskovich M. A. Handbook on Syntheses of Amino Acids: General Routes for the Syntheses of Amino Acids (Oxford University Press: New York, ed. 1, 2010
5. Groger H. Catalytic enantioselective Strecker reactions and analogous syntheses. Chem. Rev. 103, 2795-2828 (2003
6. Wang J., Liu X., & Feng X. Asymmetric Strecker reactions. Chem. Rev. 111, 6947-6983 (2011
7. Tang W., & Zhang X. New chiral phosphorus ligands for enantioselective hydrogenation. Chem. Rev. 103, 3029-3070 (2003
8. Abellan T., et al. Glycine and alanine imines as templates for asymmetric synthesis of alpha-amino acids. Eur. J. Org. Chem. 2000, 2689-2697 (2000
9. O?Donnell M. J. The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters. Acc. Chem. Res. 37, 506-517 (2004
10. Hashimoto T., & Maruoka K. Recent development and application of chiral phase-transfer catalysts. Chem. Rev. 107, 5656-5682 (2007
11. Deboves H. J. C., Montalbetti C. A. G. N., & Jackson R. F. W. Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids. J. Chem. Soc., Perkin Trans. 1, 1876-1884 (2001
12. Reddy B. V. S., Reddy L. R., & Corey E. J. Novel acetoxylation and C-C coupling reactions at unactivated positions in α -amino acid derivatives. Org. Lett. 8, 3391-3394 (2006
13. Tran L. D., & Daugulis O. Nonnatural amino acid synthesis by using carbon-hydrogen bond functionalization methodology. Angew. Chem. Int. Ed. 51, 5188-5191 (2012
14. Zhang S.-Y., Li Q., He G., Nack W. A., & Chen G. Stereoselective synthesis of β -alkylated α -amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)-H bonds with primary alkyl halides. J. Am. Chem. Soc. 135, 12135-12141 (2013
15. Zhang Q., et al. Stereoselective synthesis of chiral α -amino-β -lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp3)-H bonds. Angew. Chem. Int. Ed. 52, 13588-13592 (2013
16. Rodriguez N., Romero-Revilla J. A., Fernandez-Ibanez M. A., & Carretero J. C. Palladium-catalyzed N-(2-pyridyl)sulfonyldirected C(sp3)-H γ -arylation of amino acid derivatives. Chem. Sci. 4, 175-179 (2013
17. He J., et al. Ligand-controlled C(sp3)-H arylation and olefination in synthesis of unnatural chiral α -amino acids. Science 343, 1216-1220 (2014
18. Prier C. K., Rankic D. A., & MacMillan D. W. C. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem. Rev. 113, 5322-5363 (2013
19. Narayanam J. M. R., & Stephenson C. R. J. Visible light photoredox catalysis: applications in organic synthesis. Chem. Soc. Rev. 40, 102-113 (2011
20. Yoon T. P., Ischay M. A., & Du J. Visible light photocatalysis as a greener approach to photochemical synthesis. Nat. Chem. 2, 527-532 (2010
21. Zeitler K. Photoredox catalysis with visible light. Angew. Chem. Int. Ed. 48, 9785-9789 (2009
22. Xuan J., & Xiao W.-J. Visible-light photoredox catalysis. Angew. Chem. Int. Ed. 51, 6828-6838 (2012
23. Hari D. P., & Konig B. The photocatalyzed meerwein arylation: classic reaction of aryl diazonium salts in a new light. Angew. Chem. Int. Ed. 52, 4734-4743 (2013
24. Schnermann M. J., & Overman L. E. A concise synthesis of (-)-aplyviolene facilitated by a strategic tertiary radical conjugate addition. Angew. Chem. Int. Ed. 51, 9576-9580 (2012
25. Lackner G. L., Quasdorf K. W., & Overman L. E. Direct construction of quaternary carbons from tertiary alcohols via photoredoxcatalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates. J. Am. Chem. Soc. 135, 15342-15345 (2013
26. Lang S. B., O?Nele K. M., & Tunge J. A. Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis. J. Am. Chem. Soc. 136, 13606-13609 (2014
27. Leung J. C. T., Chatalova-Sazepin C., West J. G., Rueda-Becerril M., Paquin J.-F., & Sammis G. M. Photo-fluorodecarboxylation of 2-aryloxy and 2-aryl carboxylic acids. Angew. Chem. Int. Ed. 51, 10804-10807 (2012
28. Yang J., Zhang J., Qi L., Hu C., & Chen Y. Visible-light-induced chemoselective reductive decarboxylative alkynylation under biomolecule-compatible conditions. Chem. Commun. 51, 5275-5278 (2015
29. Noble A., & MacMillan D. W. C. Photoredox α -vinylation of α - amino acids and N-aryl amines. J. Am. Chem. Soc. 136, 11602-11605 (2014
30. Zuo Z., et al. Merging photoredox with nickel catalysis: Coupling of α -carboxyl sp3-carbons with aryl halides. Science 345, 437-440 (2014
31. Zuo Z., & MacMillan D. W. C. Decarboxylative arylation of α - amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore. J. Am. Chem. Soc. 136, 5257-5260 (2014