Supporting Information. Organocatalytic Synthesis of 4-Aryl-1,2,3,4-tetrahydropyridines from. Morita-Baylis-Hillman Carbonates through a One-Pot
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1 Supporting Information Organocatalytic Synthesis of 4-Aryl-1,2,3,4-tetrahydropyridines from Morita-Baylis-Hillman Carbonates through a One-Pot Three-Component Cyclization Jian Wei, Yuntong Li, Cheng Tao, Huifei Wang, Bin Cheng, Hongbin Zhai,*, and Yun Li*,, liyun@lzu.edu.cn; zhaihb@pkusz.edu.cn The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou , China Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen , China State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai , China List of content 1. Separation Methods for Tetrahydropyridines 6a-x and Lactams 7a and 7b.. S1-S2 2. NMR spectra S3-S58 3. X-ray of compound 6hb, 6na, 7aa and 7bb.. S59-S60
2 1. Separation Methods for Tetrahydropyridines 6a-x and Lactams 7a and 7b 6a: 6aa and 6ab were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 55:45, flow rate: 2 ml/min). 6b: 6ba and 6bb were separated by HPLC (Waters sunfire C 18, column size: mm, 10μm, water/ch 3 CN = 55:45, flow rate: 2 ml/min). 6c: 6ca and 6cb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 65:35, flow rate: 2 ml/min). 6d: 6da and 6db were separated by HPLC (Waters sunfire silica, column size: mm, 5 μm, EtOH/Hexane = 2:98, flow rate: 25 ml/min). 6e: 6ea and 6eb were separated by HPLC (Waters sunfire silica, column size: mm, 5 μm, EtOH/ Hexane = 2:98, flow rate: 25 ml/min). 6f: 6fa and 6fb were separated by chiral SFC (ChomegaChiral CCC, column size: 20 mm I.D. 250mm, 5 μm, CO 2 (liquid)/meoh (0.1% NH 4 OH) = 80:20, flow rate: 60 g/min). 6g: 6ga and 6gb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 55:45, flow rate: 2 ml/min). 6h: 6ha and 6hb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 55:45, flow rate: 2 ml/min). 6i: 6ia and 6ib were separated by HPLC (Waters sunfire silica, column size: mm, 5 μm, EtOH/ Hexane = 2:98, flow rate: 25 ml/min). 6j: 6ja and 6jb were separated by HPLC (Waters sunfire silica, column size: mm, 5 μm, EtOH/ Hexane = 2:98, flow rate: 25 ml/min). 6k: 6ka and 6kb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 70:30, flow rate: 2 ml/min). 6l: 6la and 6lb were separated by HPLC (Waters sunfire C 18, column size: mm, 5 μm, water (10 mm NH 4 HCO 3 )/CH 3 CN = 50:50, flow rate: 25 ml/min). 6m: 6ma and 6mb were separated by HPLC (Waters sunfire C 18, column size: mm, 5 μm, water (10 mm NH 4 HCO 3 )/CH 3 CN = 50:50, flow rate: 25 ml/min). 6n: 6na and 6nb were separated by HPLC (Waters sunfire C 18, column size: mm, 5 μm, water/ch 3 CN = 45:55, flow rate: 2 ml/min). 6o: 6oa and 6ob were separated by HPLC (Waters sunfire silica, column size: mm, 5 μm, EtOH/ Hexane = 2:98, flow rate: 25 ml/min). 6p: 6pa and 6pb were separated by chiral SFC (ChomegaChiral CC4, column size: 20mm I.D. 250mm, 5 μm, CO 2 (liquid)/meoh (0.1% NH 4 OH) = 80/20, flow rate: 60 g/min). 6q: 6qa and 6qb were separated by chromatography on silica gel with elution of PE/EA = 20:1. 6r: 6ra and 6rb were separated by chromatography on silica gel with elution of PE/EA = 20:1. 6s: 6sa and 6sb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 55:45, flow rate: 2 ml/min). 6t: 6ta and 6tb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 55:45, flow rate: 2 ml/min). 6u: 6ua and 6ub were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 45:55, flow rate: 2 ml/min). 6v: 6va and 6vb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 45:55, flow rate: 2 ml/min). S1
3 6w: 6wa and 6wb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 50:50, flow rate: 2 ml/min). 6x: 6xa and 6xb were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 45:55, flow rate: 2 ml/min). 7a: 7aa and 7ab were separated by HPLC (Waters sunfire C 18, column size: mm, 10 μm, water/ch 3 CN = 30:70, flow rate: 2 ml/min). 7b: 7bb could be obtained by recrystallization. S2
4 2. NMR spectra Fig. S1. 1 H NMR of compound 6aa (400 MHz, CDCl 3 ). Fig. S2. 13 C NMR of compound 6aa (100 MHz, CDCl 3 ). S3
5 Fig. S3. 1 H NMR of compound 6ab (400 MHz, CDCl 3 ). Fig. S4. 13 C NMR of compound 6ab (100 MHz, CDCl 3 ). S4
6 Fig. S5. 1 H NMR of compound 6ba (400 MHz, CDCl 3 ). Fig. S6. 13 C NMR of compound 6ba (100 MHz, CDCl 3 ). S5
7 Fig. S7. 1 H NMR of compound 6bb (400 MHz, CDCl 3 ). Fig. S8. 13 C NMR of compound 6bb (100 MHz, CDCl 3 ). S6
8 Fig. S9. 1 H NMR of compound 6ca (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ca (100 MHz, CDCl 3 ). S7
9 Fig. S11. 1 H NMR of compound 6cb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6cb (100 MHz, CDCl 3 ). S8
10 Fig. S13. 1 H NMR of compound 6da (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6da (100 MHz, CDCl 3 ). S9
11 Fig. S15. 1 H NMR of compound 6db (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6db (100 MHz, CDCl 3 ). S10
12 Fig. S17. 1 H NMR of compound 6ea (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ea (100 MHz, CDCl 3 ). S11
13 Fig. S19. 1 H NMR of compound 6eb (300 MHz, CDCl 3 ). Fig. S C NMR of compound 6eb (150 MHz, CDCl 3 ). S12
14 Fig. S21. 1 H NMR of compound 6fa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6fa (100 MHz, CDCl 3 ). S13
15 Fig. S23. 1 H NMR of compound 6fb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6fb (100 MHz, CDCl 3 ). S14
16 Fig. S25. 1 H NMR of compound 6ga (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ga (100 MHz, CDCl 3 ). S15
17 Fig. S27. 1 H NMR of compound 6gb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6gb (100 MHz, CDCl 3 ). S16
18 Fig. S29. 1 H NMR of compound 6ha (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ha (100 MHz, CDCl 3 ). S17
19 Fig. S31. 1 H NMR of compound 6hb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6hb (100 MHz, CDCl 3 ). S18
20 Fig. S33. 1 H NMR of compound 6ia (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ia (100 MHz, CDCl 3 ). S19
21 Fig. S35. 1 H NMR of compound 6ib (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ib (100 MHz, CDCl 3 ). S20
22 Fig. S37. 1 H NMR of compound 6ja (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ja (100 MHz, CDCl 3 ). S21
23 Fig. S39. 1 H NMR of compound 6jb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6jb (100 MHz, CDCl 3 ). S22
24 Fig. S41. 1 H NMR of compound 6ka (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ka (100 MHz, CDCl 3 ). S23
25 Fig. S43. 1 H NMR of compound 6kb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6kb (100 MHz, CDCl 3 ). S24
26 Fig. S45. 1 H NMR of compound 6la (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6la (100 MHz, CDCl 3 ). S25
27 Fig. S47. 1 H NMR of compound 6lb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6lb (100 MHz, CDCl 3 ). S26
28 Fig. S49. 1 H NMR of compound 6ma (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ma (100 MHz, CDCl 3 ). S27
29 Fig. S51. 1 H NMR of compound 6mb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6mb (100 MHz, CDCl 3 ). S28
30 Fig. S53. 1 H NMR of compound 6na (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6na (100 MHz, CDCl 3 ). S29
31 Fig. S55. 1 H NMR of compound 6nb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6nb (150 MHz, CDCl 3 ). S30
32 Fig. S57. 1 H NMR of compound 6oa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6oa (100 MHz, CDCl 3 ). S31
33 Fig. S59. 1 H NMR of compound 6ob (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ob (100 MHz, CDCl 3 ). S32
34 Fig. S61. 1 H NMR of compound 6pa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6pa (100 MHz, CDCl 3 ). S33
35 Fig. S63. 1 H NMR of compound 6pb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6pb (100 MHz, CDCl 3 ). S34
36 Fig. S65. 1 H NMR of compound 6qa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6qa (100 MHz, CDCl 3 ). S35
37 Fig. S67. 1 H NMR of compound 6qb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6qb (100 MHz, CDCl 3 ). S36
38 Fig. S69. 1 H NMR of compound 6ra (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ra (100 MHz, CDCl 3 ). S37
39 Fig. S71. 1 H NMR of compound 6rb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6rb (100 MHz, CDCl 3 ). S38
40 Fig. S73. 1 H NMR of compound 6sa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6sa (100 MHz, CDCl 3 ). S39
41 Fig. S75. 1 H NMR of compound 6sb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6sb (100 MHz, CDCl 3 ). S40
42 Fig. S77. 1 H NMR of compound 6ta (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ta (100 MHz, CDCl 3 ). S41
43 Fig. S79. 1 H NMR of compound 6tb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6tb (100 MHz, CDCl 3 ). S42
44 Fig. S81. 1 H NMR of compound 6ua (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ua (100 MHz, CDCl 3 ). S43
45 Fig. S83. 1 H NMR of compound 6ub (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6ub (100 MHz, CDCl 3 ). S44
46 Fig. S85. 1 H NMR of compound 6va (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6va (100 MHz, CDCl 3 ). S45
47 Fig. S87. 1 H NMR of compound 6vb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6vb (100 MHz, CDCl 3 ). S46
48 Fig. S89. 1 H NMR of compound 6wa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6wa (100 MHz, CDCl 3 ). S47
49 Fig. S91. 1 H NMR of compound 6wb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6wb (100 MHz, CDCl 3 ). S48
50 Fig. S93. 1 H NMR of compound 6xa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6xa (100 MHz, CDCl 3 ). S49
51 Fig. S95. 1 H NMR of compound 6xb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 6xb (100 MHz, CDCl 3 ). S50
52 Fig. S97. 1 H NMR of compound 6y (400 MHz, CDCl 3 ) Fig. S C NMR of compound 6y (100 MHz, CDCl 3 ). S51
53 Fig. S99. 1 H NMR of compound 7aa (400 MHz, CDCl 3 ). Fig. S C NMR of compound 7aa (100 MHz, CDCl 3 ). S52
54 Fig. S H NMR of compound 7ab (400 MHz, CDCl 3 ). Fig. S C NMR of compound 7ab (150 MHz, CDCl 3 ). S53
55 Fig. S H NMR of compound 7bb (400 MHz, CDCl 3 ). Fig. S C NMR of compound 7bb (100 MHz, CDCl 3 ). S54
56 Fig. S H NMR of compound 7b (400 MHz, CDCl 3 ). Fig. S C NMR of compound 7b (100 MHz, CDCl 3 ). S55
57 Fig. S H NMR of compound 8 (400 MHz, CDCl 3 ). Fig. S108. Selected key 3 J coupling values of compound 8 s 1 H NMR (400 MHz, CDCl 3 ). S56
58 Fig. S C NMR of compound 8 (100 MHz, CDCl 3 ). Naphthyl residue CO2Me NMe CO2Et H5a H4 H3 H5e H2 H1 CO2Et C1-Me Fig. S110. NOESY spectrum of compound 8 (400 MHz, CDCl 3 ). S57
59 CO2Me NMe Naphthyl residue CO2Et H4 H3 H5e H2 H5a H1 CO2Et C1-Me Fig. S H- 1 H COSY spectrum of compound 8 (400 MHz, CDCl 3 ). S58
60 3. X-ray of compound 6hb, 6na, 7aa and 7bb 6hb Thermal ellipsoids are drawn at the 35% probability level 6na Thermal ellipsoids are drawn at the 35% probability level S59
61 7aa Thermal ellipsoids are drawn at the 35% probability level 7bb Thermal ellipsoids are drawn at the 35% probability level The X-ray structural data were deposited at the Cambridge Crystallographic Data Center. CCDC , , and , contains the supplementary crystallographic data. S60
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