A Chiral Thiourea as Template for Enantioselective. Intramolecular [2+2] Photocycloaddition Reactions
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1 A Chiral Thiourea as Template for Enantioselective Intramolecular [2+2] Photocycloaddition Reactions Supporting Information Florian Mayr, 1 Richard Brimioulle, 1 Thorsten Bach 1* 1 Department Chemie and Catalysis Research Center (CRC), Technische Universität München, Lichtenbergstr. 4, Garching, Germany Content 1. Screening for thioureas and reaction conditions NMR-spectra of new compounds HPLC- and chiral GC data of enantioenriched products Data for enantioselective reactions at λ = 366 nm Data for sensitized enantioselective reactions at λ = 419 nm
2 1. Screening for thioureas and reaction conditions Table 1: Screening of different literature known thioureas. entry thiourea time [min] 7 [%] ee [%] n.d k
3 Table 2: Screening of different solvents for photoreaction with thiourea 5k. Entry solvent t [min] 7 [%] ee [%] 1 PhCH PhCF ,3-(CF 3 ) 2 Ph PhH CH 2 Cl (CH 2 Cl) Et 2 O Table 3: Solvent screening at low temperature entry solvent T [ C] 7 [%] ee [%] 1 PhCH CH 2 Cl PhCF PhCF 3 :1,3-(CF 3 ) 2 Ph 1:2)
4 Table 4: Screening for loading of 5k at low temperature Entry 5k [mol%] t [h] 7 [%] ee [%] table 5: Screening of different concentrations at low temperature Entry c [mm] t [h] 7 [%] ee [%]
5 2. NMR-spectra of new compounds 5
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44 NMR spectra of substrate 6 and thiourea 5k in benzene-d 6 and combination of both with 50 mol% and 100 mol% of 5k. 44
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52 3. HPLC- and chiral GC data of enantioenriched products 3.1 Data for enantioselective reactions at λ = 366 nm 52
53 52 FM-MW-08-I Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM-MW-08-I Injection Volume: 10,0 Vial Number: RB4 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: Säule1_NP_ISO_90_10_1_50 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :06 Sample Weight: 1,0000 Run Time (min): 50,00 Sample Amount: 1, F-Mayr #52 FM-MW-08-I UV_VIS_1 mau WVL:210 nm 1-16, , min 15,0 16,3 17,5 18,8 20,0 21,3 22,5 23,8 25,0 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 16,92 n.a. 109,367 51,670 50,12 n.a. BMB 2 22,12 n.a. 82,561 51,414 49,88 n.a. BMB Total: 191, , ,00 0,000 53
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59 65 FM-FP-18 Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM-FP-18 Injection Volume: 10,0 Vial Number: GD2 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: An3_Säule1_ISO_90_10_0_0_1_30 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :45 Sample Weight: 1,0000 Run Time (min): 30,00 Sample Amount: 1, Mayr #65 FM-FP-18 UV_VIS_1 mau WVL:210 nm 1-17, , min 15,0 16,3 17,5 18,8 20,0 21,3 22,5 23,8 25,0 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 17,30 n.a. 322, ,304 43,06 n.a. BMB 2 21,99 n.a. 315, ,350 56,94 n.a. BMB Total: 637, , ,00 0,000 59
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67 3.2 Data for sensitized enantioselective reactions at λ = 419 nm 67
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69 57 FM-490-II Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM-490-II Injection Volume: 10,0 Vial Number: GB8 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: An3_Säule1_ISO_90_10_0_0_1_30 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :09 Sample Weight: 1,0000 Run Time (min): 30,00 Sample Amount: 1, ,0 Mayr #57 [modified by HPLC-Admin] FM-490-II UV_VIS_1 mau 2-23,097 WVL:210 nm 62,5 50,0 37,5 25,0 1-18,121 12,5-10,0 min 15,0 16,3 17,5 18,8 20,0 21,3 22,5 23,8 25,0 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 18,12 n.a. 15,568 6,601 12,50 n.a. BMB* 2 23,10 n.a. 74,310 46,203 87,50 n.a. BMB Total: 89,879 52, ,00 0,000 69
70 32 FM-MR-29-III Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM-MR-29-III Injection Volume: 10,0 Vial Number: RD4 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: An3_Säule1_ISO_90_10_0_0_1_30 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :45 Sample Weight: 1,0000 Run Time (min): 30,00 Sample Amount: 1, Mayr #32 FM-MR-29-III UV_VIS_1 mau WVL:210 nm 1-13, , min 10,0 11,3 12,5 13,8 15,0 16,3 17,5 18,8 20,0 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 13,72 n.a. 176,824 66,732 50,04 n.a. BMB 2 16,40 n.a. 151,334 66,623 49,96 n.a. BMB Total: 328, , ,00 0,000 70
71 68 FM-496-II Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM-496-II Injection Volume: 10,0 Vial Number: GD6 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: An3_Säule1_ISO_90_10_0_0_1_30 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :55 Sample Weight: 1,0000 Run Time (min): 30,00 Sample Amount: 1, Mayr #68 [modified by HPLC-Admin] FM-496-II UV_VIS_1 mau WVL:210 nm , , min 10,0 11,3 12,5 13,8 15,0 16,3 17,5 18,8 20,0 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 14,00 n.a. 49,316 18,070 13,87 n.a. BMB* 2 16,40 n.a. 239, ,173 86,13 n.a. BMB* Total: 288, , ,00 0,000 71
72 48 FM-251-II Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM-251-II Injection Volume: 5,0 Vial Number: BE2 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: Säule1_NP_ISO_80_20_1_50 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :35 Sample Weight: 1,0000 Run Time (min): 50,00 Sample Amount: 1, F-Mayr #48 FM-251-II UV_VIS_1 mau WVL:210 nm 1-12, , min 10,00 11,00 12,00 13,00 14,00 15,00 16,00 17,00 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 12,05 n.a. 411, ,579 52,95 n.a. BM 2 13,38 n.a. 327, ,793 47,05 n.a. MB Total: 738, , ,00 0,000 72
73 50 FM295-II Daicel Chiralpak, AD-H, 250x4.6 Sample Name: FM295-II Injection Volume: 5,0 Vial Number: BA6 Channel: UV_VIS_1 Sample Type: unknown Wavelength: Control Program: Säule1_NP_ISO_80_20_1_30 Bandwidth: 1 Quantif. Method: grada Dilution Factor: 1,0000 Recording Time: :56 Sample Weight: 1,0000 Run Time (min): 30,00 Sample Amount: 1, F-Mayr #50 FM295-II UV_VIS_1 mau WVL:210 nm 1-12, , min 10,00 11,00 12,00 13,00 14,00 15,00 16,00 17,00 No. Ret.Time Peak Name Height Area Rel.Area Amount Type min mau mau*min % 1 12,26 n.a. 215,256 76,487 50,40 n.a. BM 2 13,60 n.a. 190,298 75,276 49,60 n.a. MB Total: 405, , ,00 0,000 73
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