doi: 10.1021/ja501621q.
Epub 2014 Mar 31.
Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore
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- PMID: 24712922
- PMCID: PMC4004246
- DOI: 10.1021/ja501621q
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Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore
J Am Chem Soc.
.
Abstract
The direct decarboxylative arylation of α-amino acids has been achieved via visible light-mediated photoredox catalysis. This method offers rapid entry to prevalent benzylic amine architectures from an abundant biomass, specifically α-amino acid precursors. Significant substrate scope is observed with respect to both the amino acid and arene components.
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References
-
- Lehninger A. L.; Nelson D. L.; Cox M. M.. Principles of Biochemistry; Worth Publishers: New York, 1993.
- Walsh C.Enzymatic Reaction Mechanisms; W. H. Freeman and Co.: New York, 1979.
- van Poelje P. D.; Snell E. E. Annu. Rev. Biochem. 1990, 59, 29. - PubMed
-
- Vijh A. K.; Conway B. E. Chem. Rev. 1967, 67, 623.
- Johnson R. G.; Ingham R. K. Chem. Rev. 1956, 56, 219.
- Sheldon R. A.; Kochi J. K. Org. React. 1972, 19, 279.
- Barton D. H. R.; Crich D.; Motherwell W. B. Tetrahedron 1985, 41, 3901.
-
- Kolbe H. Liebigs Ann. Chem. 1849, 69, 257.
-
- Hunsdiecker H.; Hunsdiecker C. Chem. Ber. 1942, 75B, 291.
-
- Barton D. H. R.; Serebryakov E. P. Proc. Chem. Soc. 1962, 309.
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