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1 UPPRTING INFRMATIN ynthesis of sulfur-containing exo-bicyclic dienes and their Diels-Alder reactions to access thiacycle-fused polycyclic systems Thomas Castanheiro, a Angèle choenfelder, a Morgan Donnard, a Isabelle Chataigner, b,c and Mihaela Gulea a * a Université de trasbourg, CNR, Laboratoire d Innovation Thérapeutique, LIT UMR 7200, trasbourg, France b Normandie Université, INA Rouen, CNR, CBRA UMR 6014, Rouen, France c orbonne Université, UPMC Univ. Paris 6, CNR UMR 7616 Laboratoire de Chimie Théorique Paris, France Table of contents: 1. X-ray structures 2 2. Theoretical study Total energy and cartesian coordinates for D1, 3b, 3f Cycloaddition between D1 and 3b Cycloaddition between D1 and 3f Computed conformations for 10fA-major, 10fB-minor Validation of the DFT methods for cycloaddition of 3b and D H and 13 C NMR spectra 31
2 1. X-ray structures of 4bA, 4 ca, 4fA, and 8b CCDC , , and contain the supplementary crystallographic data for this paper. These data are provided free of charge by the Cambridge Crystallographic Data Centre. 4bA: CCDC ; Formula: C19 H18 3 1; Unit Cell Parameters: a (6) b (6) c (4) P31c Bond precision: C-C = A Wavelength= Cell: a= (6) b= (6) c=8.4256(4) alpha=90 beta=90 gamma=120 Temperature: 173 K Calculated Reported Volume (2) (19) pace group P 3 1 c P 3 1 c Hall group P 3-2c P 3-2c Moiety formula C19 H18 3 C19 H18 3 um formula C19 H18 3 C19 H18 3 Mr Dx,g cm Z 6 6 Mu (mm-1) F F000' h,k,lmax 21,21,10 21,20,10 Nref 2774[ 1396] 2451 Tmin,Tmax 0.890, ,0.753 Tmin' Correction method= # Reported T Limits: Tmin=0.651 Tmax=0.753 AbsCorr = MULTI-CAN Data completeness= 1.76/0.88 Theta(max)= R(reflections)= ( 2128) wr2(reflections)= ( 2451) = Npar= 208
3 Figure 1. X-ray structure of 4bA (R1 = 3.7%) 4 ca: CCDC ; Formula: C14 H16 4 1; Unit Cell Parameters: a (3) b (7) c (4) P21/c Bond precision: C-C = A Wavelength= Cell: a=8.1274(3) b= (7) c=8.9072(4) alpha=90 beta= (1) gamma=90 Temperature: 173 K Calculated Reported Volume (9) (9) pace group P 21/c P 21/c Hall group -P 2ybc -P 2ybc Moiety formula C14 H16 4 C14 H16 4 um formula C14 H16 4 C14 H16 4 Mr Dx,g cm Z 4 4 Mu (mm-1) F F000' h,k,lmax 12,26,13 12,26,13 Nref Tmin,Tmax 0.922, ,0.747 Tmin' Correction method= # Reported T Limits: Tmin=0.702 Tmax=0.747 AbsCorr = MULTI-CAN Data completeness= Theta(max)= R(reflections)= ( 3771) wr2(reflections)= ( 4631) = Npar= 176
4 Figure 2. X-ray structure of 4 ca (R1 = 4.0%) Crystals obtained from 4fA were of lower quality, however it was possible to get the X-ray structure. 4fA: CCDC ; Formula: C20 H20 3 1; Unit Cell Parameters: a (5) b (2) c (16) Pbca Bond precision: C-C = A Wavelength= Cell: a= (5) b=7.6426(2) c= (16) alpha=90 beta=90 gamma=90 Temperature: 173 K Calculated Reported Volume (2) (2) pace group P b c a P b c a Hall group -P 2ac 2ab -P 2ac 2ab Moiety formula C20 H20 3 C20 H20 3 um formula C20 H20 3 C20 H20 3 Mr Dx,g cm Z 8 8 Mu (mm-1) F F000' h,k,lmax 14,9,48 14,9,48 Nref Tmin,Tmax 0.964,0.991 Tmin' Correction method= not given
5 Data completeness= Theta(max)= R(reflections)= ( 1999) wr2(reflections)= ( 3559) = Npar= 217 Figure 3. X-ray structure of 4fA (R1 = 11%) 8b: CCDC ; Formula: C23 H19 N3 2 1; Unit Cell Parameters: a (10) b (4) c (10) P21/c Bond precision: C-C = A Wavelength= Cell: a=8.6858(1) b= (4) c=8.4200(1) alpha=90 beta=93.074(1) gamma=90 Temperature: 173 K Calculated Reported Volume (4) (4) pace group P 21/c P 21/c Hall group -P 2ybc -P 2ybc Moiety formula C23 H19 N3 2 C23 H19 N3 2 um formula C23 H19 N3 2 C23 H19 N3 2 Mr Dx,g cm Z 4 4 Mu (mm-1) F F000' h,k,lmax 11,32,10 11,32,10 Nref Tmin,Tmax 0.908,0.960 Tmin' Correction method= Not given
6 Data completeness= Theta(max)= R(reflections)= ( 3585) wr2(reflections)= ( 4230) = Npar= 262 Figure 4. X-ray structure of 8b (R1 = 4.3%)
7 2. Theoretical study 2.1. Total energy and cartesian coordinates for D1, 3b, 3f, Figure 5. D1 Electronic Energy = a.u. um of electronic and thermal free energies = a.u. Number of imaginary frequencies: 0 C C H H C C Figure 6. 3b Electronic Energy = a.u. um of electronic and thermal free energies = a.u. Number of imaginary frequencies: 0 C C C C C C C C C C C C C
8 C C H H H H H H H H H H H H H H H H
9 Figure 7. 3f Electronic Energy = a.u. um of electronic and thermal free energies = a.u. Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H
10 2.2. Cycloaddition between D1 and 3b Figure 8. T_5_top_endo Electronic Energy = a.u. (DE e = 4.83 kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H
11 H Figure 9. cycloadduct_5_top_endo Electronic Energy = a.u. (ΔE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (ΔG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H
12 H H H Figure 10. T_5_below_endo Electronic Energy = a.u. (DE e = 8.73 kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H
13 H H H H H Figure 11. cycloadduct_5_below_endo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H
14 H H H H H
15 Figure 12. T_5_top_exo Electronic Energy = a.u. (DE e = 8.15 kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H
16 Figure 13. cycloadduct_5_top_exo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H C C C C H H
17 Figure 14. T_5_below_exo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H C C C C H H
18 Figure 15. cycloadduct_5_below_exo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H
19 2.3. Cycloaddition between D1 and 3f Figure 16. T_6_top_endo Electronic Energy = a.u. (DE e = 7.96 kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C H C C C C C C C H H H H H C C C C C C C C H H H H H H H H H H H
20 H H H Figure 17. cycloadduct_6_top_endo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H
21 H H H C H H Figure 18. T_6_below_endo Electronic Energy = a.u. (DE e = 9.80 kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H
22 H H H H H H H H Figure 19. cycloadduct_6_below_endo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H
23 H H H H H H H H H H Figure 20. T_6_top_exo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C H H H H C C C C C C C C C C C C H H H
24 H H H H H H H H H H H H H Figure 21. cycloadduct_6_top_exo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C H H H H H H
25 H H H H H H H H H H H H C H H Figure 22. T_6_below_exo Electronic Energy = a.u. (DE e = 8.80 kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG = kcal.mol -1 ) Number of imaginary frequencies: 1 ( ) C C C C C C C C H H H H C C C C C C C C C C C C
26 H H H H H H H H H H H H H H H H Figure 23. cycloadduct_6_below_exo Electronic Energy = a.u. (DE e = kcal.mol -1 ) um of electronic and thermal free energies = a.u. (DG r = kcal.mol -1 ) Number of imaginary frequencies: 0 C C C C C C C C C C C C C C C C C C C C
27 H H H H H H H H H H H H H H H H H H H H
28 2.4. Computed conformations for 10fA-major, 10fB-minor Figure 24. Computed conformation for 10fA-major (two views)
29 Figure 25. Computed conformation for 10fB-minor (two views)
30 30
31 1 H and 13 C NMR spectra s 31
32 Ac Br 1 s 32
33 Ac Br 1 s 33
34 Br 2a s 34
35 Br 2a s 35
36 Br 2b s 36
37 Br 2b s 37
38 Br H 2c s 38
39 2c s 39
40 Br 2d s 40
41 Br 2d s 41
42 Br 2e s 42
43 Br 2e s 43
44 Br 2f s 44
45 Br 2f s 45
46 3a s 46
47 3a s 47
48 3b s 48
49 3b s 49
50 3c s 50
51 3c s 51
52 3d s 52
53 3d s 53
54 DMF 3e (impure, used directly in cycloaddi=on) CH 2 Cl 2 s 54
55 3f s 55
56 3f s 56
57 4aA + minor Ra=o 10/3 s 57
58 + minor 4aA Ra=o 10/3 s 58
59 5aA N s 59
60 5aA N s 60
61 6aA C 2 Me C 2 Me 6aB C 2 Me C 2 Me Ra=o 10/3 s 61
62 6aA C 2 Me C 2 Me 6aB C 2 Me C 2 Me Ra=o 10/3 s 62
63 N 7aA Et N N Ph s 63
64 N 7aA Et N N Ph s 64
65 8a N Et N N Ph s 65
66 8a N Et N N Ph s 66
67 ? 9a Me N 10a Me N Mixture of 2 products in 3/1 ra=o s 67
68 ? 9a Me N 10a Me N Mixture of 2 products in 3/1 ra=o s 68
69 4bA s 69
70 4bA s 70
71 5bA N s 71
72 5bA N s 72
73 7bA N N N s 73
74 7bA N N N s 74
75 8b N N N s 75
76 8b N N N s 76
77 + minor N 10b (major) Ra=o 10/1 s 77
78 10b (major) N + minor Ra=o 10/1 s 78
79 4 ca C 2 H s 79
80 4 ca C 2 H s 80
81 4dA s 81
82 4dA s 82
83 Me Me 6dA C 2 Me C 2 Me 6dB ra=o 2/1 C 2 Me C 2 Me Ra=o 2/10 s 83
84 Me Me 6dA C 2 Me C 2 Me 6dB ra=o 2/1 C 2 Me C 2 Me Ra=o 2/10 s 84
85 7dA Me N N N Ph + minor Ra=o 20/1 s 85
86 7dA Me N N N Ph + minor Ra=o 20/1 s 86
87 7eA N N N s 87
88 N N N 7eA s 88
89 Ph 4fA s 89
90 Ph 4fA s 90
91 Ph 7fA N N N Ph s 91
92 Ph 7fA N N N Ph s 92
93 Ph Ph 2-Py 10fA (Major) Me Ra=o 10/3 2-Py 10fA (minor) Me s 93
94 Ph Ph 2-Py 10fA (Major) Me Ra=o 10/3 2-Py 10fA (minor) Me s 94
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