One-pot chemoenzymatic synthesis of chiral disubstituted 1,2,3-triazoles in aqueous media

Journal of Molecular Catalysis B: Enzymatic

Volumn 91, Issue , 2013, Pages 93-97

  De Souza De Oliveira, Camila ^a   De Andrade, Kleber Tellini ^a   Omori, Alvaro Takeo ^a  

^a UNIVERSIDADE FEDERAL DO ABC   (Brazil)

Author keywords

Daucus carota Biocatalysis Click chemistry Water chemistry

Indexed keywords

BIOCATALYSTS;

1 ,2 ,3-TRIAZOLES; 1 ,3-DIPOLARCYCLOADDITION; AQUEOUS MEDIA; BIOCATALYSIS; CHEMO-ENZYMATIC SYNTHESIS; ENANTIOSELECTIVE REDUCTION; REACTION UNDER; TWO-STEP PROCEDURE;

STEREOCHEMISTRY;

1,2,3 TRIAZOLE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BIOCATALYST; CARROT; CATALYSIS; CHIRALITY; CLICK CHEMISTRY; CYCLOADDITION; ENANTIOSELECTIVITY; ONE POT SYNTHESIS; ORGANIC CHEMISTRY;

DAUCUS CAROTA;

EID: 84875536405     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2013.03.004     Document Type: Letter

References (25)

1. A. Bruggink, R. Schoevart, and T. Kieboom Org. Process Res. Dev. 7 2003 622 640
2. J.C. Wasilke, S.J. Obrey, T. Baker, and G.C. Bazan Chem. Rev. 105 2005 1001 1020
3. J.E. Moses, and A.D. Moorhouse Chem. Soc. Rev. 36 2007 1249 1262
4. K.B. Sharpless, V.V. Rostovtsev, L.G. Green, and V.V. Fokin Angew. Chem. Int. Ed. 41 2002 2596 2599
5. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952 3015
6. H.C. Kolb, and K.B. Sharpless Drug Discov. Today 8 2003 1128 1137
7. S.G. Agalave, S.R. Maujan, and V.S. Pore Chem. Asian J. 6 2011 2696 2718
8. A.J. McCarroll, C.S. Matthews, G. Wells, T.D. Bradshaw, and M.F.G. Stevens Org. Biomol. Chem 8 2010 2078 2084
9. G. Aromí, L.A. Barrios, O. Roubeau, and P. Gamez Coord. Chem. Rev. 255 2011 485 546
10. Y.H. Lau, P.J. Rutledge, M. Watkinson, and M.H. Todd Chem. Soc. Rev. 40 2011 2848 2866
11. J.-F. Lutz Angew. Chem. Int. Ed. 46 2007 1018 1025
12. P. Rodriguez, M. Barton, V. Aldabalde, S. Onetto, P. Panizza, P. Menendez, D. Gonzalez, and S. Rodriguez J. Mol. Catal. B: Enzym. 49 2007 8 11
13. P. Rodriguez, B. Reyes, M. Barton, C. Coronel, P. Menendez, D. Gonzalez, and S. Rodriguez J. Mol. Catal. B: Enzym. 71 2011 90 94
14. N. Blanchard, and P. van de Weghe Org. Biomol. Chem. 4 2006 2348 2353 and references therein
15. G.A. Cordell, T.L.G. Lemos, F.J.Q. Monte, and M.C. Mattos J. Nat. Prod. 70 2007 478 492
16. Recent uses of warrD. carota bits as biocatalyst M.S. Salvano, J.J. Cantero, A.M. Vazquez, S.M. Formica, and M.L. Aimar J. Mol. Catal. B: Enzym. 71 2011 16 21
17. R. Lacheretz, D.G. Pardo, and J. Cossy Org. Lett. 11 2009 1245 1248
18. H.M.C. Ferraz, G.G. Bianco, F.I. Bombonato, L.H. Andrade, and A.L.M. Porto Quim. Nova 31 2008 813 817
19. A.C. Marr, and S. Liu Trends Biotechnol. 29 2011 199 204
20. J.V. Comasseto, A.T. Omori, A.L.M. Porto, and L.H. Andrade Tetrahedron Lett. 45 2004 473 476
21. M. Warrier, F.K. Lo, H.G. Monbouquette, and A.M.G. Garibay Photochem. Photobiol. Sci. 3 2004 859 863
22. The absolute configuration of (S)-1-(3-azidophenyl)ethanol was assigned by comparison of the sign of the measured optical rotation of the corresponding amine (after chemical conversion by Staudinger reaction) with those of the literature T.S. Kaufman, and V.L. Ponzo Synlett 7 2002 1128 1130
23. For the (S)-1-(4-azidophenyl)ethanol, the azido group was converted into the acetamide: A. Kamal, A.V. Ramana, K.S. Reddy, K.V. Ramana, A.H. Babu, and B.R. Prasad Tetrahedron Lett. 45 2004 8187 8190
24. and the sign of the measured optical rotation was compared with the literature: J. Wettergren, A. Bogevig, M. Portier, and H. Adolfson Adv. Synth. Catal. 348 2006 1277 1282
25. V. Prelog Pure Appl. Chem. 9 1964 119 130