Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes

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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α, β-unsaturated Aldehydes Supporting Information Contents: 1. Preparation of substrates S2 2. X-ray structure of compound 3a S5 3. NMR Spectra S7 4. HPLC Profiles S43 S1

2 Preparation of substrates To a solution of thiazolidine-2,4-dione (0.61 g, 5.2 mmol, 1.0 equiv) in dry toluene (12.0 ml) was added Lawesson s reagent (2.2 g, 5.2 mmol, 1.0 equiv). The reaction mixture was refluxed for 2 h and cooled to room temperature. The solid was filtered off and crystallized from acetone to afford isorhodanine (0.64 g, 98% yield) as a yellow crystal. 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), 4.67 (s, 2H); MS (ESI) m/z: [M+H] +. To a solution of isorhodanine (0.60 g, 4.5 mmol, 1.0 equiv) in DMF (10.0 ml) was added NaH (0.19 g, 4.9 mmol, 1.1 equiv) and the mixture was stirred for 0.5 h at 0 C. Then, iodomethane (0.75 g, 4.5 mmol, 1.0 equiv) was added and the reaction mixture was stirred for 1 h. Water (30.0 ml) was added to the reaction mixture and extracted by ethyl acetate (15.0 ml 3). The organic layer was dried over Na 2 SO 4, and concentrated to give the crude product, which was further purified by column chromatography to yield the desired substrate 2a. The synthetic method for substrates 2b-k was similar to the synthesis of substrate 2a. For substrate 2l, 2 equivalent of iodomethane was used. 4-(Methylthio)thiazol-2(3H)-one (2a). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), 6.26 (s, 1H), 2.41 (s, 3H); 13 C NMR (150 MHz, CDCl 3, TMS): δ = , , , 17.08; HRMS (ESI) calcd for C 4 H 6 NO 2 S 2 [M+H] + = , found (Ethylthio)thiazol-2(3H)-one (2b). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), (m, 1H), 2.85 (dd, J = 7.0, 14.6 Hz, 2H), 1.19 (t, J = 7.5 Hz, 3H); 13 C NMR (150 MHz, DMSO-d 6, TMS): δ = , , , 27.64, 14.75; HRMS (ESI) calcd for C 5 H 8 NOS 2 [M+H] + = , found ((Naphthalen-2-ylmethyl)thio)thiazol-2(3H)-one (2c). 1 H NMR (600 MHz, CDCl 3, TMS): δ = 9.67 (s, 1H), (m, 2H), (m, 1H), 7.62 (s, 1H), (m, 2H), 7.40 (dd, J = 1.8, 8.4 Hz, 1H), 6.03 (s, 1H), 4.13 (s, 2H); 13 C NMR (150 MHz, DMSO-d 6, TMS) δ = , , , , S2

3 127.25, , , , 39.72, 29.20; HRMS (ESI) calcd for C 14 H 12 NOS 2 [M+H] + = , found ((3-Fluorobenzyl)thio)thiazol-2(3H)-one (2d). 1 H NMR (600 MHz,CDCl 3, TMS): δ = (s, 1H), (m, 1H), (m, 3H), 6.08 (s, 1H), 3.97 (s, 2H); 13 C NMR (150 MHz, CDCl 3, TMS): δ = , , , , , , , 24.56, , , , , , , , 39.11, 39.08; HRMS (ESI) calcd for C 10 H 7 FNOS 2 [M-H] - = , found ((2-Methylbenzyl)thio)thiazol-2(3H)-one (2e). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), (m, 2H), (m, 2H), 6.29 (d, J = 1.7 Hz, 1H), 4.09 (s, 2H), 2.32 (s, 3H); 13 C NMR (150 MHz, DMSO-d 6, TMS): δ = , , , , , , , , , 36.44, 19.14; HRMS (ESI) calcd for C 11 H 12 NOS 2 [M+H] + = , found ((4-Methylbenzyl)thio)thiazol-2(3H)-one (2f). 1 H NMR (300 MHz, DMSO-d 6, TMS): δ = (s, 1H), 7.11 (s, 4H), 6.27 (d, J = 1.8 Hz, 1H), 4.05 (s, 2H), 2.26 (s, 3H); 13 C NMR (75 MHz, DMSO-d 6, TMS): δ = , , , , , , , 37.54, 21.18; HRMS (ESI) calcd for C 11 H 12 NOS 2 [M+H] + = , found ((2-Nitrobenzyl)thio)thiazol-2(3H)-one (2g). 1 H NMR (500 MHz, DMSO-d 6, TMS): δ = (s, 1H), 8.04 (dd, J = 1.1, 8.1 Hz, 1H), 7.68 (td, J = 1.2, 7.5, 15.2 Hz, 1H), 7.55 (td, J = 1.3, 8.2, 15.5 Hz, 1H), 7.38 (dd, J = 1.2, 7.7 Hz, 1H), 6.27 (d, J = 1.6 Hz, 1H), 4.35 (s, 2H), 13 C NMR (125 MHz, DMSO-d 6, TMS) δ = , , , , , , , , , 35.53; HRMS (ESI) calcd for C 10 H 7 N 2 O 3 S 2 [M-H] - = , found ((4-Nitrobenzyl)thio)thiazol-2(3H)-one (2h). 1 H NMR (500 MHz, DMSO-d 6, TMS): δ = (s, 1H), 8.19 (d, J = 9.1 Hz, 2H), 7.49 (d, J = 9.1 Hz, 2H), 6.30 (d, J = 0.9 Hz, 1H), 4.22 (s, 2H); 13 C NMR (125 MHz, DMSO-d 6, S3

4 TMS): δ = , , , , , , , 37.05; HRMS (ESI) calcd for C 10 H 7 N 2 O 3 S 2 [M-H] - = , found (((2-Oxo-2,3-dihydrothiazol-4-yl)thio)methyl)benzonitrile (2i). 1 H NMR (300 MHz, DMSO-d 6, TMS): δ = (s, 1H), 7.81 (d, J = 8.1 Hz, 2H), 7.42 (d, J = 8.2 Hz, 2H), 6.32 (d, J = 1.3 Hz, 1H), 4.18 (s, 2H); 13 C NMR (75 MHz, DMSO-d 6, TMS): δ = , , , , , , , 37.32; HRMS (ESI) calcd for C 11 H 9 N 2 OS 2 [M+H] - = , found ((4-(Tert-butyl)benzyl)thio)thiazol-2(3H)-one (2j). 1 H NMR (300 MHz, DMSO-d 6, TMS): δ = (s, 1H), 7.33 (d, J = 8.3 Hz, 2H), 7.17 (d, J = 8.3 Hz, 2H), 6.31 (d, J = 1.6 Hz, 1H), 4.10 (s, 2H), 1.24 (s, 9H); 13 C NMR (75 MHz, DMSO-d 6, TMS): δ = , , , , , , , 37.38, 34.69, 31.56; HRMS (ESI) calcd for C 14 H 18 NOS 2 [M+H] + = , found ((2-Oxo-2,3-dihydrothiazol-4-yl)thio)acetonitrile (2k). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), 6.80 (s, 1H), 4.06 (s, 1H); 13 C NMR (150 MHz, DMSO-d 6, TMS): δ = 175.5, , , , 41.33; HRMS (ESI) calcd for C 5 H 3 N 2 OS 2 [M-H] - = , found Methyl-4-(methylthio)thiazol-2(3H)-one (2l). 1 H NMR (600 MHz, CDCl 3, TMS): δ = 7.27 (s, 1H), 6.04 (s, 1H), 3.33 (s,3h), 2.36 (s, 3H); HRMS (ESI) calcd for C 5 H 8 NOS 2 [M+H] + = , found S4

5 X-ray structure of 3a Table 1. Crystal data and structure refinement for 3a. Identification code Empirical formula mo_21229a C19H19NO2S2 Formula weight Temperature Wavelength Crystal system, space group 296(2) K Å Orthorhombic, P2(1)2(1)2(1) Unit cell dimensions a = (13) Å alpha = 90 deg. b = (15) Å c = (18) Å Volume (4) Å 3 Z, Calculated density 4, Mg/m 3 Absorption coefficient mm -1 beta = 90 deg. gamma = 90 deg. F(000) 752 Crystal size Theta range for data collection Limiting indices 0.12 x 0.11 x 0.09 mm 2.24 to deg. -14<=h<=14, -14<=k<=14, -19<=l<=16 Reflections collected / unique / 4244 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4244 / 1 / 225 S5

6 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Absolute structure parameter 0.00(12) Largest diff. peak and hole and e. Å -3 S6

7 NMR Spectra Compound 3a S7

8 Compound 3b S8

9 Compound 3c S9

10 Compound 3d S10

11 Compound 3e S11

12 Compound 3f S12

13 Compound 3g S13

14 Compound 3h S14

15 Compound 3i S15

16 Compound 3j S16

17 Compound 3k S17

18 Compound 3l S18

19 Compound 3m S19

20 Compound 4a S20

21 Compound 4b S21

22 Compound 4c S22

23 Compound 4d S23

24 Compound 4e S24

25 Compound 4f S25

26 Compound 4g S26

27 Compound 4h S27

28 Compound 4i S28

29 Compound 4j S29

30 Compound 4k S30

31 Compound 2a S31

32 Compound 2b S32

33 Compound 2c S33

34 Compound 2d S34

35 Compound 2e S35

36 Compound 2f S36

37 Compound 2g S37

38 Compound 2h S38

39 Compound 2i S39

40 Compound 2j S40

41 Compound 2k S41

42 Compound 2l S42

43 HPLC Chromatograms Compound 3a S43

44 Compound 3b S44

45 Compound 3c S45

46 Compound 3d S46

47 Compound 3e S47

48 Compound 3f S48

49 Compound 3g S49

50 Compound 3h S50

51 Compound 3i S51

52 Compound 3j S52

53 Compound 3k S53

54 Compound 3l S54

55 Compound 3m S55

56 Compound 4a S56

57 Compound 4b S57

58 Compound 4c S58

59 Compound 4d S59

60 Compound 4e S60

61 Compound 4f S61

62 Compound 4g S62

63 Compound 4h S63

64 Compound 4i S64

65 Compound 4j S65

66 Compound 4k S66

IV. ANHANG 179. Anhang 178

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