Supporting Information. Two Catalytic Methods of an Asymmetric Wittig [2,3]-Rearrangement
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1 Supporting Information Two Catalytic Methods of an Asymmetric Wittig [2,3]-Rearrangement Maksim Ošeka, Mariliis Kimm, Ivar Järving, Kristin Lippur, and Tõnis Kanger * Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, Tallinn, Estonia List of Contents (1) NMR spectra for catalysts III HCl, IV HCl, V HCl and VII S2 (2) Additional optimization of Ca-catalyzed Wittig [2,3]-rearrangement reaction S6 (3) NMR and HRMS study of complex formation from ligand L1 and Ca(NTf 2 ) 2 S7 (4) NMR spectra for compounds 1 and 2 S10 (5) Chiral HPLC chromatograms for compounds 2 S35 S1
2 (1) NMR spectra for catalysts III HCl, IV HCl, V HCl and VII 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of III HCl S2
3 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of IV HCl S3
4 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of V HCl S4
5 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of VII S5
6 (2) Additional optimization of Ca-catalyzed Wittig [2,3]-rearrangement reaction MeO 2 C MeO 2 C O 1a Ph L1,CaCl 2 additionalbase solvent, temp Ph MeO 2 C MeO 2 C OH 2a Table S1. Screening of solvents in the presence or absence of imidazole a Entry Base Solvent Temp. ( C) Reaction time Conversion (%) b ee % c 1 MeOH RT 24 h 0 2 MeOH 60 3 d Imidazole MeOH 60 3 d EtOH RT 24 h 0 5 Imidazole EtOH 60 3 d propanol 60 3 d Imidazole 2-propanol 60 3 d Imidazole THF 60 3 d 6 9 Imidazole CHCl d 7 10 d Imidazole tbuoh 60 3 d Imidazole HFIP e h 0 a Reaction conditions: 1a (0.1 mmol), L1 (5 mol%), CaCl 2 (5 mol%) and base (5 mol%) in the corresponding solvent (1 ml) was stirred at indicated temperature. b Conversion was determined by 1 H NMR. c Enantiomeric excess was determined by chiral HPLC. d Reaction conditions: 1a (0.1 mmol), L1 (5 mol%), Ca(NTf 2 ) 2 (5 mol%) and imidazole (5 mol%) in tbuoh (1 ml) was stirred at 60 C. e HFIP = 1,1,1,3,3,3-hexafluoro-2-propanol. S6
7 (3) NMR and HRMS study of complex formation from ligand L1 and Ca(NTf 2 ) 2 Complexation study of ligand L1 with Ca(NTf 2 ) 2 by 1 H NMR was performed at room temperature in CDCl 3 under air. The results of the study are shown on figure S1. From conditions B we can see, that the catalyst preparation is completed with 1:1 ratio of the calcium salt and ligand. From condition C, we do not see any signals of the free ligand. Broad peaks reveal a possible ligand exchange process. From conditions D and E can be observed, that both imidazole and 2-propanol take part in the forementioned complex formation. The experimental data (Table S1) confirm the incorporation of imidazole into the complex. The reaction without imidazole is slower and also less selective than in the presence of that base (Table S1, entries 6 and 7). A L1; B L1:Ca(NTf 2 ) 2 (1:1); C L1:Ca(NTf 2 ) 2 (2:1); D L1:Ca(NTf 2 ) 2 :imidazole (1:1:1); E L1:Ca(NTf 2 ) 2 :imidazole:2-propanol (1:1:1:10); F L1:Ca(NTf 2 ) 2 :imidazole:2-propanol:compound 1 (1:1:1:10:5). S7
8 A B C D E F Figure S1. Complexation study of Ca(NTf 2 ) 2 and ligand L1 by 1 H NMR. Figure S2. ESI-MS, Gas 50 C; Sample: 1a (0.05 mmol), L1 (0.01 mmol), Ca(NTf 2 ) 2 (0.01 mmol), imidazole (0.01 mmol), 2-propanol (1 ml). S8
9 Figure S3. ESI-MS, Gas 300 C; Sample: 1a (0.05 mmol), L1 (0.01 mmol), Ca(NTf 2 ) 2 (0.01 mmol), imidazole (0.01 mmol), 2-propanol (1 ml). The HRMS peak correlates to the following structure: S9
10 (4) NMR spectra for compounds 1 and 2 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1a S10
11 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1b S11
12 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1c S12
13 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1d S13
14 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1e S14
15 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1f S15
16 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1g S16
17 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1h S17
18 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1i S18
19 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1j S19
20 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1k S20
21 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1l S21
22 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1m S22
23 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 1n S23
24 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2a obtained by method A S24
25 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2d obtained by method A S25
26 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2e obtained by method A S26
27 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2f obtained by method B S27
28 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2h obtained by method A S28
29 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2i obtained by method A S29
30 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2j obtained by method A S30
31 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2k obtained by method A S31
32 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2l obtained by method A NO 2 MeO 2 C MeO 2 C OH 2l NO 2 MeO 2 C MeO 2 C OH 2l S32
33 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2m obtained by method A S33
34 1 H (400 MHz, CDCl 3 ) and 13 C spectra (101 MHz, CDCl 3 ) of 2n obtained by method A S34
35 (5) Chiral HPLC chromatograms for compounds 2 HPLC chromatogram of rac-2a and (R)-2a obtained by method A S35
36 HPLC chromatogram of rac-2d and (S)-2d obtained by method B S36
37 HPLC chromatogram of rac-2f and enant-2f obtained by method B S37
38 HPLC chromatogram of rac-2h and (R)-2h obtained by method A S38
39 HPLC chromatogram of rac-2i and (R)-2i obtained by method A S39
40 HPLC chromatogram of rac-2j and (R)-2j obtained by method A S40
41 HPLC chromatogram of rac-2k and (R)-2k obtained by method A S41
42 HPLC chromatogram of rac-2l and (S)-2l obtained by method B S42
43 HPLC chromatogram of rac-2m and (R)-2m obtained by method A S43
44 HPLC chromatogram of rac-2n and (S)-2n obtained by method B S44
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