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Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition of thiols to imines under mild conditions Tábata B. Albuquerque, Caren D. G. da ilva, Aline R. de liveira, Beatriz F. dos antos, Beatriz A. L. da ilva, Ramesh Katla, Mariana P. D. Rocha and Nelson L. C. Domingues*. GENERAL PRCEDURE.... EXPERIMENTAL PRCEDURE..... General Procedure for N-Boc-Imines..... General Procedure for addition thiols to N-Boc-Imines.... H AND C NMR PECTRA ANALYI.... GENERAL PRCEDURE All other reactions were carried out using chemical reagents and solvents without any specific treatment. The respective reactions were monitored by Thin Layer Chromatography (TLC) MACHEREY-NAGEL (IL G / UV ) and were visualized by fluorescence quenching with UV light at nm. The purification of the compounds was performed by chromatography on silica gel (eluent: hexane/etac, :). H and C NMR spectra were recorded in CDCl on Bruker ( MHz and 7 MHz respectively) spectrometer. H NMR data are reported as follows: chemical shift (δ, ppm), multiplicity (s = singlet, d = doublet, q =quartet, m = multiplet), coupling constants (J) and assignment. The infrared spectra were recorded spectra were recorded on FT/IR type A spectrometer of Jasco.

. EXPERIMENTAL PRCEDURE.. General Procedure for N-Boc-Imines + Na + NH HCH ºC, h HN Ph In a ml bottle flask was added aldehyde (.7 mmol), benzenesulfinic acid sodium salt (.7 mmol), tert-butyl carbamate (.7 mmol) e HC H (7 µl). The mixture was magnetically stirred in CH H ( ml) and water ( ml) at room temperature for hours. After completed, the solid was filtrated and washed with ether and dried overnight (yield %). Previous literature reference Wang, H. Y, Zhang, J. X, Cao, D. D and Zhao, G. Enantioselective Addition of Thiols to Imines Catalyzed by Thiourea Quaternary Ammonium alts. AC Catalysis, (), 8-... General Procedure for addition thiols to N-Boc-Imines HN Ph + H,g LLP DME, K C, r.t. HN a a a In a ml bottle flask was added thiol (. mmol), imine (. mmol), K C (. mmol) and,g LLP in DME ( ml) at room temperature. The reaction was magnetically stirred and the reaction was monitored by TLC (eluent: hexane/ EtAc, :). When the reaction was completed, the enzyme was separated by filtration off and the mixture was extracted with DCM (x ml). The organic layers were combined, dried over anhydrous Na, the salt was filtered off and organic phase was concentrated under reduced pressure. The product was purified by column chromatography on silica gel (eluent: hexane/ EtAc, :) to afford the product.

. H AND C NMR PECTRA ANALYI tert-butyl (phenyl(phenylthio)methyl)carbamate: White solid. MW:. g/mol. C 8 H N. IR (KBr) (ν máx cm - ): 8,, 8,, 8,, 87, 8, 78. H NMR ( MHz, CDCl ): δ ppm. (s, H),.-. (d, J= Hz, H),.-. (d, J= Hz, H), 7.-7. (m, H). C NMR (7 MHz, CDCl ): δ ppm 8.7,.,., 7.7, 8., 8., 8., 8.,.,.,.,.7,.. tert-butyl (((-fluorophenyl)thio(phenyl)methyl)carbamate: F White solid. MW:. g/mol. C 8 H FN. IR KBr (ν máx cm - ):, 88,,, 87, 8,, 88, 8. H NMR ( MHz, DM): δ ppm. (s, H),.-. (d, J =, H),.-. (d, J= Hz, H), 7.-7. (m, H). C NMR (7 MHz, CDCl ): δ ppm 8., 8.,.,., 8.8, 8.,.,.7,.,.77-. (d, J C-F =.). tert-butyl (((-chlorophenyl)thio)(phenyl)methyl)carbamate: White solid, MW:. g/mol. C 8 H ClN. IR (KBr) (ν máx cm - ): 8, 8,, 7, 87,,,,,, 88. H NMR ( MHz, CDCl ): δ ppm. (s, H),.-. (d, J =, H),.-. (d, J= Hz, H), 7.-7. (m, H). C NMR (7 MHz, CDCl ): δ ppm 8.8,.,.7,.7,.,., 7.8,., Cl.7,.,.,.,.7,.8,.. tert-butyl (phenyl(p-tolylthio)methyl)carbamate: White solid. MW:. g/mol. C H N. IR KBr (ν máx cm - ):,, 8,,, 7,, 87, 8. H NMR ( MHz, CDCl ): δ ppm. (s, H),. (s, H),.-. (d, J = Hz, H),.-. (d, J= Hz, H),.7-7. (m, H). C NMR (7 MHz, CDCl ): δ ppm., 8.8,.,., 7., 8., 8., 8.8,.,.8,.7,.7.

tert-butyl (((-methoxyphenyl)thio)(phenyl)methyl)carbamate: White solid. MW:. g/mol. C H N. IR KBr (ν máx cm - ): 7, 8, 8,,,, 8,, 87, 8. H NMR ( MHz, CDCl ): δ ppm. (s, H),.8 (s, H),.-. (d, J = Hz, H),.-. (d, J= Hz, H),.8-7. (m, H). C NMR ( MHz, CDCl ): δ ppm 8.,.8,.,.,., 8.7, 8., 8.8,.,.7,.,.8,.,.,.7. tert-butyl ((benzylthio)(phenyl)methyl)carbamate: White solid. MW:. g/mol. C H N. IR KBr (ν máx cm - ): 7, 8, 8,,,, 8,, 87, 8. H NMR ( MHz, CDCl ): δ ppm.8 (s, H),.7-.8 (m, H),.7-. (d, J= Hz),.77-.8 (m, H),.87-7. (m, H). C NMR ( MHz, CDCl ): δ ppm 8.,., 8.,., 7., 7., 7., 8.7, 8., 8., 8., 8.8,.,.7,.. tert-butyl ((-nitrophenyl)(phenylthio)methyl)carbamate: N White solid. MW:. g/mol. C 8 H N. IR KBr (ν máx cm - ): 8,, 8,,,, 7,,, 88, 8. H NMR ( MHz, CDCl ): δ ppm.7 (s, H),.-. (d, J= Hz, H),.7-. (d, J= Hz, H), 7.-7. (m, H). C NMR ( MHz, CDCl ): δ ppm 8.8, 8.,.7,.,.7, 8., 8.7,.8,.8,.7,.7,.,.8,., 8.7. tert-butyl ((-methoxyphenyl)(phenylthio)methyl)carbamate: White solid. MW:. g/mol. C H N. IR KBr (ν máx cm - ):,, 8, 7,,,,, 88, 87. H NMR ( MHz, CDCl ): δ ppm,. (s, H),.8 (s, H),.-. (d, J= Hz, H),.-. (d, J= Hz, H),.87-7. (m, H). C NMR (7 MHz, CDCl ): δ ppm 8.,.,.8,.7,.,.7, 7.7, 8.7,.,.,.7,.,.,..

tert-butyl (-(phenylthio)butyl)carbamate: White solid. MW: 8. g/mol. C H N. IR KBr (ν máx cm - ): 7, 8, 8,,,, 8,, 87, 8. H NMR ( MHz, CDCl ): δ ppm.-. (m, H),. (s, H),.-. (m, H),.-.7 (m, H),.7-. (d, J= Hz, H),.-.7 (dd, J= Hz, H), 7.-7.7 (m, H). C NMR ( MHz, CDCl ): δ ppm.,., 8.,.7, 8., 8.8, 7., 8.8,.,.8,.,.. Figure. FTIR spectra for the tert-butyl (phenyl(phenylthio)methyl)carbamate. 7 %T Wavenumber [cm-]

Fitted pectrum 7. 7. 7. 7. 7. 7. 7. 7. 7.8 7. 7. 7. 7. 7. 7.8..... 8 8 8..7.7. - 8 7 - Figure. H NMR spectra for the tert-butyl (phenyl(phenylthio)methyl)carbamate...7... 8. 8. 8. 8. 7.7. 77. 77. 7.8. 8.7 E+7 E+7 E+7 E+7 E+7 E+7 E+7 E+7 E+7 E+ 8E+ 7E+ E+ E+ E+ E+ E+ E+ -E+ -E+ 8 7 8 7 Figure. C NMR spectra for the tert-butyl (phenyl(phenylthio)methyl)carbamate. -

7. 7. 7. 7. 7. 7. 7. 7. 7. 7.8 7. 7. 7. 7. 7. 7. 7.8..... 8 8 F 8 8..7.7. - 8 7 - Figure. H NMR spectra for the tert-butyl (((-fluorophenyl)thio(phenyl)methyl)carbamate...77..7. 8. 8.8. 77. 77. 7.. 8. 8. F 8 7 8 7 - Figure. C NMR spectra for the tert-butyl (((-fluorophenyl)thio(phenyl)methyl)carbamate.

m 7. 7. 7. 7. 7. 7. 7. 7. 7. 7.8 7. 7. 7. 7. 7. 7. 7.8..... 8 8 Cl 8.8.7.8.8-8 7 - Figure. H NMR spectra for the tert-butyl (((-chlorophenyl)thio(phenyl)methyl)carbamate...8.7....7. 7.8...7 8.7 7. 77. 77. 7..7. 8.8 8 8 Cl 8-8 7 8 7 - Figure 7. C NMR spectra for the tert-butyl (((-chlorophenyl)thiol(phenyl)methyl)carbamate.

7. 7.8 7. 7. 7. 7. 7.8 7. 7. 7. 7. 7. 7. 7. 7. 7. 7..7..... -. 8 7 8 7.7.... - 8 7 - Figure 8. H NMR spectra for the tert-butyl (phenyl)(p-tolylthio)methyl)carbamate. metiltiofenol KMI - C Vicente - DQI.7.7.8. 8.8 8. 8. 7.. 77. 7.87 7.. 8.8. -. 8 7 8 7 8 7 - Figure. C NMR spectra for the tert-butyl (phenyl)(p-tolylthio)methyl)carbamate.

m 7. 7. 7. 7. 7. 7. 7. 7. 7.7 7. 7. 7. 7. 7. 7. 7.8.87.87.8.8.8.8.8.....8. E+ E+ E+ E+ E+ E+ E+ 8 7..7.7.8.7. - - 8 7 - Figure. H NMR spectra for the tert-butyl (((-methoxyphenyl)thio)(phenyl)methyl)carbamate. Fitted pectrum.7...8..7. 8.8 8. 8.7... 77. 77. 7.8..8 8. 8 7 - - - 8 7 8 7 Figure. C NMR spectra for the tert-butyl (((-methoxyphenyl)thio)(phenyl)methyl)carbamate.

7. 7.7 7. 7. 7. 7. 7.8 7. 7. 7.8 7. 7..8.7..87.87.8.8.77..7.8.8.7.7.8 -. 8 8 8..8.8..8.7-8 7 - - Figure. H NMR spectra for the tert-butyl ((benzylthio)(phenyl)methyl)carbamate. Fitted pectrum...7. 8.8 8. 8. 8. 8.7 7. 7. 7.. 77.8 77. 7.77 8.. 8. 8 8 8-7 8 7 Figure. C NMR spectra for the tert-butyl ((benzylthio)(phenyl)methyl)carbamate.

Fitted pectrum 7. 7. 7. 7. 7. 7. 7.7 7. 7. 7. 7. 7. 7...7...7 -. N Figure. H NMR spectra for the tert-butyl ((-nitrophenyl)(phenylthio)methyl)carbamate. 8.7..8..7.7.8.8. 8.7 8..7 77.7 77. 7.77..7 8. 8.8.....7.8-7 8 7 - - 8 N 7 8 7 8 7 Figure. H NMR spectra for the tert-butyl ((-nitrophenyl)(phenylthio)methyl)carbamate.

7. 7.8 7. 7. 7. 7. 7. 7. 7.7..87...8..8. 8 8 8.8..7.. - 8 7 - Figure. H NMR spectra for the tert-butyl ((-methoxyphenyl)(phenylthio)methyl)carbamate.....7.. 8.7 7.7.7..7 78.8 77. 77. 7.7 7.8.8. 8. 8 8 8 8-8 7 8 7 - Figure 7. CNMR spectra for the tert-butyl ((-methoxyphenyl)(phenylthio)methyl)carbamate.

a 7.7 7. 7. 7. 7.8 7..7....7..7.7.7.7......7.......7.....7.8.7-8 7 - - Figure 8. H NMR spectra for the tert-butyl (-(phenylthio)butyl)carbamate....8. 8.8 7. 7.77 77.7 77. 7.7 8.8 8..7 8... 8 7 8 7 Figure. H NMR spectra for the tert-butyl (-(phenylthio)butyl)carbamate.

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