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Synthesis 2016; 48(18): 3077-3086
DOI: 10.1055/s-0035-1561628
DOI: 10.1055/s-0035-1561628
paper
Synthesis of Fluorescent Amino Acids via Palladium-Catalyzed Allylic Alkylations
Further Information
Publication History
Received: 11 February 2016
Accepted after revision: 06 April 2016
Publication Date:
19 May 2016 (online)
Abstract
Coumarin-derived allylic carbonates are found to be suitable electrophiles for the synthesis of fluorescent amino acids via palladium-catalyzed allylic alkylation of chelated glycine enolates. The formation of regioisomers can be suppressed by proper choice of the allyl carbonate.
Supporting Information
- Supporting information for this article (copies of NMR spectra) is available online at http://dx.doi.org/10.1055/s-0035-1561628.
- Supporting Information
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References
- 1a Valeur B, Brochon J.-C. New Trends in Fluorescence Spectroscopy: Applications to Chemical and Life Sciences. Springer; Berlin: 2001
- 1b Goldys EM. Fluorescence applications in biotechnology and life science. Wiley; Hoboken, New Jersey: 2009
- 2a Hama Y, Urano Y, Koyama Y, Gunn AJ, Choyke PL, Kobayashi H. Clin. Cancer Res. 2007; 13: 6335
- 2b Dillingham MS, Wallace MI. Org. Biomol.Chem. 2008; 6: 3031
- 2c Neef AB, Schultz C. Angew. Chem. Int. Ed. 2009; 48: 1498 ; Angew. Chem. 2009, 121, 1526
- 3 Maeda M. Laser Dyes. Academic Press; New York: 1984
- 4 Yee DY, Balsanek V, Sames D. J. Am. Chem. Soc. 2004; 126: 2282
- 5 McFarland JM, Francis MB. J. Am. Chem. Soc. 2005; 127: 13490
- 6a Bernardes GJ. L, Chalker JM, Errey JC, Davis BG. J. Am. Chem. Soc. 2008; 130: 5052
- 6b Dondoni A. Angew. Chem. Int. Ed. 2008; 47: 8995 ; Angew. Chem. 2008, 120, 9133
- 6c Triola G, Brunsveld L, Waldmann H. J. Org. Chem. 2008; 73: 3646
- 6d Wittrock S, Becker T, Kunz H. Angew. Chem. Int. Ed. 2007; 46: 5226 ; Angew. Chem. 2007, 119, 5319
- 6e Jonkheijm P, Weinrich D, Köhn M, Engelkamp H, Christianen PC. M, Kuhlmann J, Maan JC, Nüsse D, Schröder H, Wacker R, Breinbauer R, Niemeyer CM, Waldmann H. Angew. Chem. Int. Ed. 2008; 47: 4421 ; Angew. Chem. 2008, 120, 4493
- 7a Kodadek T, Duroux-Richard I, Bonnafous JC. Trends Pharmacol. Sci. 2005; 26: 210
- 7b McFarland JM, Joshi NS, Francis MB. J. Am. Chem. Soc. 2008; 130: 7639
- 7c Tilley SD, Francis MB. J. Am. Chem. Soc. 2006; 128: 1080
- 8a Sharpless KB, van der Eycken E. QSAR Comb. Sci. 2007; 26: 1110
- 8b Wirtz L, Auerbach D, Jung G, Kazmaier U. Synthesis 2012; 44: 2005
- 9a Quirin C, Kazmaier U. Eur. J. Org. Chem. 2009; 371
- 9b Ullrich A, Chai Y, Pistorius D, Elnakady YA, Herrmann J, Weissman KJ, Kazmaier U, Müller R. Angew. Chem. Int. Ed. 2009; 47: 4422 ; Angew. Chem. 2009, 121, 4486
- 9c Ullrich A, Herrmann J, Müller R, Kazmaier U. Eur. J. Org. Chem. 2009; 6367
- 9d Karmann L, Schulz K, Herrmann J, Müller R, Kazmaier U. Angew. Chem. Int. Ed. 2015; 54: 4502 ; Angew. Chem. 2015, 127, 4585
- 10a Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565 ; Angew. Chem. 1963, 75, 604
-
10b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596 ; Angew. Chem. 2002, 114, 2708
- 10c Tornoe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
-
10d Chan TR, Hilgraf R, Sharpless KB, Fokin VV. Org. Lett. 2004; 6: 2853
- 10e Rodionov VO, Presolski SI, Diaz DD, Fokin VV, Finn MG. J. Am. Chem. Soc. 2007; 129: 12705
- 11a Kazmaier U, Schneider C. Synlett 1996; 975
- 11b Grandel R, Kazmaier U. Tetrahedron Lett. 1997; 38: 8009
- 12a Pohlman M, Kazmaier U. Org. Lett. 2003; 5: 2631
- 12b Pohlman M, Kazmaier U, Lindner T. J. Org. Chem. 2004; 69: 6909
- 13a Kazmaier U. Current Org. Chem. 2003; 7: 317
- 13b Kazmaier U, Lindner T. Angew. Chem. Int. Ed. 2005; 44: 3303 ; Angew. Chem. 2005, 117, 3368
- 13c Kazmaier U, Stolz D, Krämer K, Zumpe F. Chem. Eur. J. 2008; 14: 1322
- 14a Bayer A, Kazmaier U. Org. Lett. 2010; 12: 4960
- 14b Bayer A, Kazmaier U. Chem. Eur. J. 2014; 20: 10484
- 14c Bayer A, Kazmaier U. J. Org. Chem. 2014; 79: 8491
- 14d Bayer A, Kazmaier U. J. Org. Chem. 2014; 79: 8498
- 15a Kazmaier U, Stolz D. Angew. Chem. Int. Ed. 2006; 45: 3072 ; Angew. Chem. 2006, 118, 3143
- 15b Stolz D, Kazmaier U. Synthesis 2008; 2288
- 16a Kazmaier U, Deska J, Watzke A. Angew. Chem. Int. Ed. 2006; 45: 4855 ; Angew. Chem. 2006, 118, 4973
- 16b Deska J, Kazmaier U. Angew. Chem. Int. Ed. 2007; 46: 4570 ; Angew. Chem. 2007, 119, 4654
- 16c Deska J, Kazmaier U. Chem. Eur. J. 2007; 13: 6204
- 16d Deska J, Kazmaier U. Curr. Org. Chem. 2008; 12: 355
- 17 Wang T, Zhao Y, Shi M, Wu F. Dyes Pigments 2007; 75: 104
- 18 Zhang D, Zhu L, Li H, Su J. Front. Chem. China 2010; 5: 241
- 19 Szabo KJ. Chem. Soc. Rev. 2001; 30: 136
- 20a Wang J, Xie J, Schultz PG. J. Am. Chem. Soc. 2006; 128: 8738
- 20b Wang J, Xie J, Schultz PG. Patent WO2007139870, 2007
- 21 Akrawi OA, Nagy GZ, Panonay T, Villinger A, Langer P. Tetrahedron Lett. 2012; 53: 3206
- 22 Elsinghorst PW, Härtig W, Goldhammer S, Groscheb J, Gütschow M. Org. Biomol. Chem. 2009; 7: 3940
- 23 Gogoi N, Boruwa J, Barua NC. Eur. J. Org. Chem. 2006; 1722
- 24 Zhang Q, Xu W, Lu X. J. Org. Chem. 2005; 70: 1505