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Alfonso, I., Astorga, C., Rebolledo, F. and Gotor, V. (1996). Sequential biocatalytic resolution of (±)-trans-cyclohexane-1,2-diamine. Chemoenzymic synthesis of an optically active polyamine. Chem. Commun. 2471–2472.
Alfonso, I. and Gotor, V. (2004). Biocatalytic and biomimetic aminolysis reactions: useful tools for selective transformations on polifunctional substrates. Chem. Soc. Rev. 33, 201–209.
Badjić, J.D., Kadnikova E.N. and Kostić, N.M. (2001). Enantioselective aminolysis of an α-chloroester catalyzed by Candida cylindracea lipase encapsuled in sol-gel silica glass. Org. Lett. 3, 2025–2027.
Breen, G.F. (2004). Enzymatic resolution of a secondary amine using novel acylating reagents. Tetrahedron: Asymmetry 15, 1427–1430.
Bornscheuer, U.T. and Kazlauskas R.J. (2004). Catalytic promiscuity in biocatalysis: Using old enzymes to form new bonds and follow new pathways. Angew. Chem. Int. Ed. 43, 6032–6040.
Bouzemi, N., Debbeche, H., Aribi-Zouiou, L. and Fiaud, J-C. (2004). On the use of succinic anhydride as acylating agent for practical resolution of aryl-alkyl alcohols through lipase-catalysed acylation. Tetrahedron Lett. 45, 627–630.
Branneby, C., Carlqvist, P., Magnusson, A., Hult, K., Brinck, T. and Berglund, P. (2003). Carbon-Carbon bonds by hydrolytic enzymes. J. Am. Chem. Soc. 125, 874–875.
Branneby, C., Carlqvist, P., Hult, K., Brinck, T. and Berglund, P. (2004). Aldol additions with mutant lipase: analysis by experiments and theoretical calculations. J. Mol. Catal. B: Enz. 31, 123–128.
Carlqvist, P., Svedendahl M., Branneby, C., Hult, K., Brinck, T. and Berglund, P. (2004). Exploring the active-site of a rationally redesigned lipase for catalysis of Michael-type additions. ChemBioChem 6, 331–336.
Choi, Y.K., Kim, M.J., Ahn, Y. and Kim M-J. (2001). Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines. Org. Lett. 3, 4099–4101.
De Gonzalo, G., Brieva, R., Sànchez, V., Bayod, M. and Gotor, V. (2003). Anhydrides as acylating agents in the enzymatic resolution of an intermediate of (-)-paroxetine. J. Org. Chem. 68, 3333–3336.
Faber, K. Biotransformations in Organic Chemistry. Springer-Verlag: Heidelberg, 2004
Fernàndez-Solares, L., Dìaz, M., Brieva, R., Sànchez, V.M., Bayod, M. and Gotor, V. (2002). Enzymatic resolution of new carbonate intermediates for the synthesis of (S)-(±)-zopiclone. Tetrahedron: Asymmetry 13, 2577–2582.
Ferrero, M. and Gotor, V. (2000). Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides and C-nucleosides. Chem. Rev. 100, 4319–4347.
Garcìa-Urdiales, E., Alfonso, I. and Gotor, V. (2005). Enantioselective desymmetrization in organic synthesis. Chem. Rev. 105, 313–354.
Ghanem A. and Aboul-Enein H.Y. (2004). Lipase mediated chiral resolution of racemates in organic solvents. Tetrahedron: Asymmetry 15, 3331–3351.
Gonzàlez-Sabìn, J., Gotor, V. and Rebolledo, F. (2002). CAL-B-catalyzed resolution of some pharmacologically interesting β-substituted isopropylamines. Tetrahedron: Asymmetry 13, 1315–1320.
Gonzàlez-Sabin, J., Gotor, V. and F. Rebolledo, F. (2004). Chemoenzymatic preparation of optically active β-aminocyclohexanols and their application in the enantioselecetive addition of diethylzinc to benzaldehyde. Tetrahedron: Asymmetry 15, 1335–1341.
Gotor, V. (1999). Non-Conventional Hydrolase Chemistry: Amide and Carbamate Bond Formation Catalyzed by Lipases. Bioorg. Med. Chem. 7, 2189–2197.
Gotor, V. (2002). Biocatalysis applied to the preparation of pharmaceuticals. Org. Proc. Res. Dev. 6, 420–426.
Homann, M.J., Vail, R., Morgan, B., Sabesan, V., Levy, C., Dodds, D.R. and Zaks, A. (2001). Enzymatic Hydrolysis of a Prochiral 3-Substituted Glutarate Ester, an Intermediate in the Synthesis of an NK1/NK2 Dual Antagonist Adv. Synth. Catal. 343, 744–749.
Irimescu, R. and Kato, K. (2004). Lipase-catalyzed enantioselective reaction of amines with carboxylic acids under reduced pressure in non-solvent system and in ionic liquids. Tetrahedron Lett. 45, 523–525.
Jain, N., Kumar, A., Chauhan, S. and Chauhan, S.M.S. (2005). Chemical and biochemical transformations in ionic liquids. Tetrahedron 61, 1015–1060.
Kamal, A., Khanna, G.B.R. and Ramu, R. (2002). Chemoenzymatic synthesis of both enantiomers of fluoxetine, tomoxetine and nisoxetine: lipase catalysed resolution of 3-aryl-3-hydroxypropanenitriles. Tetrahedron: Asymmetry 13, 2039–2051.
Kazlauskas, R.J., Weissfloch, A.N.E Rappaport A.T. and Cuccia, L.A. (1991). A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J. Org. Chem. 56, 2656–2665.
Kazlauskas, R.J. (2005). Enhancing catalytic promiscuity for biocatalysis. Curr. Opin. Chem. Biol. 9, 195–201.
Kielbasinski, P., Zurawinski, R., Albrycht, M. and Mikolajczyk, M. (2003). The first enzymatic desymmetrizations of prochiral phosphine oxides. Tetrahedron: Asymmetry 14, 3379–3384.
Kirihara, M., Kawasaki, M., Takuwa, T., Kakuda, H., Wakikawa, T., Takeuchi, Y. and Kirk, K.L. (2003). Efficient synthesis of (R)- and (S)-1-amino-2,2-difluorocyclopropanecarboxylic acid via lipase-catalyzed desymmetrization of prochiral precursors. Tetrahedron: Asymmetry 14, 1753–1761.
Klibanov, A.M. (2001) Improving enzymes by using them in organic solvents. Nature 409, 241–246.
Krishna, S.H., Persson, M., Bornscheuer, U.T. (2002). Enantioselective transesterification of a tertiary alcohol by lipase A from Candida antarctica. Tetrahedron: Asymmetry 13, 2693–2696.
Liljeblad, A., Lindborg, J., Kanerva, A., Katajisto, J. and Kanerva, L.T. (2002). Enantioselective lipase-catalyzed reactions of methyl pipecolinate: transesterification and N-acylation. Tetrahedron Lett. 43, 2471–2474.
Liu, H.-L., Helge, B. and Anthonsen, T. Chemoenzymatic synthesis of the non-tricyclic antidepressants Fluoxetine, Tomoxetine and Nisoxetine. (2000). J. Chem. Soc. Perkin Trans. 1, 1767–1769.
Lòpez-Garcìa, M., Alfonso, I., Gotor, V. (2003a). Desymmetrization of dimethyl 3-substituted glutarates through enzymatic ammonolysis and aminolysis reactions. Tetrahedron: Asymmetry 14, 603–609.
Lòpez-Garcìa, M., Alfonso, I. and Gotor, V. (2003b). Synthesis of (R)-3,4-diaminobutanoic acid by desymmetrization of dimethyl 3-(benzylamino)glutarate through enzymatic ammonolysis. J. Org. Chem. 68, 648–651.
Luna, A., Maestro, A., Astorga, C. and Gotor, V. (1999). Enzymatic resolution of (±)-cis and (±)-trans-1-aminoindan-2-ol and (±)-cis and (±)-trans-2-aminoindan-1-ol Tetrahedron: Asymmetry 10, 1969–1977.
Luna, A., I. Alfonso, I. and Gotor, V. (2002). Biocatalytic approaches toward the synthesis of both enantiomers of trans-cyclopentane-1,2-diamine. Org. Lett. 4, 3627–3629.
Madeira Lau, R., Rantwijk, F.V., Seddon, K.R. and Sheldon R.A. (2000). Lipase-catalyzed reaction in ionic liquids. Org. Lett. 2, 4189–4191.
Morgan, B., Zaks, A., Dodds, D.R., Liu, J., Jain, R.,Megati, S., Njoroge F.J. and Girijavallabhan, V.M. (2000). Enzymatic kinetic resolution of piperidine atropoisomers: synthesis of a key intermediate of the farnesyl protein transferase inhibitor. J. Org. Chem. 65, 5451–5459.
Neri, C. and Williams, J.M.J. (2003). New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies. Adv. Synth. Catal. 345, 835–848.
Pàmies, O. and Bäckvall, J.-E. (2001). Dynamic kinetic resolution of β-azido alcohols. An efficient route to chiral aziridines and β-aminoalcohols. J. Org. Chem. 66, 4022–4025.
Pàmies, O. and Bäckvall, J-E. (2003). Combination of enzymes and metal catalysis. A powerful approach in asymmetric catalysis. Chem. Rev. 103, 3247–3262.
Puertas, S., Rebolledo, F., Gotor, V. (1996). Enantioselective enzymic aminolysis and ammonolysis of dimethyl 3-hydroxyglutarate. Synthesis of (R)-4-amino-3-hydroxybutanoic acid. J. Org. Chem. 61, 6024–6027.
Reetz, M.T. and Schimossek, K. (1996). Lipase-catalyzed dynamic kinetic resolution of chiral amines: Use of palladium as the racemization catalyst. Chimia 50, 668–669.
Sanfilippo, C., Nicolosi, G., Fabbri, D. and Dettori, M.A. (2003). Access to optically active 2,2‵-dihydroxy-6,6‵-dimethoxy-1,1‵-biphenyl by a simple biocatalytic procedure. Tetrahedron: Asymmetry 14, 3267–3270.
Takayama, S., Lee, S.T., Hung, S-H., Wong, C-H. (1999). Designing enzymic resolution of amines. Chem. Commun. 127–128.
Torre, O., Alfonso, I. and Gotor, V. (2004). Lipase catalysed Michael addition of secondary amines to acrylonitrile. Chem. Commun. 1724–1725.
van Rantwijk, F. and Sheldon, R.A. (2004). Enantioselective acylation of chiral amines catalysed by serine hydrolases. Tetrahedron 60, 501–519.
Xu, J-M., Yao, S-P., Wu, W-B., Lv, D-S and Lin X-F. (2005). Two-step sequential synthesis of pyrimidine derivatives containing a sugar branch via combining of enzymatic Michael addition/acylation. J. Mol. Catal. B: Enz. 35, 122–127.
Wiktelius, D. (2005). Lipases - Enzymes for biocatalytic asymmetric synthesis. Synlett 2111–2114.
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Gotor-Fernández, V., Vicente, G. (2007). Use of Lipases in Organic Synthesis. In: Polaina, J., MacCabe, A.P. (eds) Industrial Enzymes. Springer, Dordrecht. https://doi.org/10.1007/1-4020-5377-0_18
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