Table of contents. Ling-Yan Chen, a,b Stéphane Guillarme, a and Christine Saluzzo a *

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1 Supplementary Material Dianhydrohexitols: new tools for organocatalysis. Application in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes Ling-Yan Chen, a,b Stéphane Guillarme, a and Christine Saluzzo a * a IMMM, MS, UMR CRS 6283, Faculté des Sciences, Université du Maine, Av.. Messiaen, Le Mans Cedex 09, France b College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, , China Christine.saluzzo@univ-lemans.fr Table of contents MR data 1 MR spectrum of compound 7: S3 13 C MR spectrum of compound 7: S4 1 MR spectrum of compound 8: S5 13 C MR spectrum of compound 8: S6 1 MR spectrum of compound 9: S7 13 C MR spectrum of compound 9: S8 1 MR spectrum of compound 10: S9 13 C MR spectrum of compound 10: S10 1 MR spectrum of compound 6: S11 13 C MR spectrum of compound 6: S12 1 MR spectrum of compound 1: S13 13 C MR spectrum of compound 1: S14 1 MR spectrum of compound 2: S14 13 C MR spectrum of compound 2: S15 1 MR spectrum of compound 3: S16 13 C MR spectrum of compound 3: S17 1 MR spectrum of compound 4: S18 13 C MR spectrum of compound 4: S19 1 MR spectrum of compound 5: S20 13 C MR spectrum of compound 5: S21 1 MR spectrum of compound 14a: S22 13 C MR spectrum of compound 14a: S23 Page S1

2 1 MR spectrum of compound 14b: S24 13 C MR spectrum of compound 14b: S25 1 MR spectrum of compound 14c: S26 13 C MR spectrum of compound 14c: S27 1 MR spectrum of compound 14d: S28 13 C MR spectrum of compound 14d: S29 1 MR spectrum of compound 14e: S30 13 C MR spectrum of compound 14e: S31 1 MR spectrum of compound 14f: S32 13 C MR spectrum of compound 14f: S33 1 MR spectrum of compound 14g: S34 13 C MR spectrum of compound 14g: S35 1 MR spectrum of compound 14h: S36 13 C MR spectrum of compound 14h: S37 Catalytic enantioselective Friedel-Crafts alkylation in the presence of thiourea catalyst 2: PLC chromatograms Formation of compound 14a: S38 Formation of compound 14a: S39 Formation of compound 14b: S39 Formation of compound 14b: S40 Formation of compound 14c: S40 Formation of compound 14c: S41 Formation of compound 14d: S41 Formation of compound 14d: S42 Formation of compound 14e: S43 Formation of compound 14f: S44 Formation of compound 14g: S45 Formation of compound 14g: S46 Formation of compound 14h: S46 Formation of compound 14h: S47 Page S2

3 MR Spectra Ts Ts Page S3

4 Ts Ts Page S4

5 3 3 Page S5

6 3 3 Page S6

7 2 2 Page S7

8 2 2 Page S8

9 3 3 Page S9

10 3 3 Page S10

11 F 3 C S CF 3 F 3 C S CF 3 Page S11

12 F 3 C S CF 3 F 3 C S CF 3 Page S12

13 2 S CF 3 CF 3 Page S13

14 2 S CF 3 CF 3 F 3 C S CF 3 F 3 C S C F 3 Page S14

15 F 3 C S CF 3 F 3 C S C F 3 Page S15

16 S S Page S16

17 S S Page S17

18 S S Page S18

19 S S Page S19

20 S CF 3 S 2 CF 3 Page S20

21 S CF 3 S 2 CF 3 Page S21

22 Page S22

23 Page S23

24 Page S24

25 Page S25

26 Page S26

27 Page S27

28 Page S28

29 Page S29

30 Page S30

31 Page S31

32 Page S32

33 Page S33

34 Page S34

35 Page S35

36 Page S36

37 Page S37

38 PLC Data Ph * 14a 2 Page S38

39 Ph * 14a 2 Me * 2 14b Page S39

40 Me * 2 14b Br * 2 14c Page S40

41 Br * 2 14c * 2 Cl 14d Page S41

42 * 2 Cl 14d Page S42

43 * 2 F 14e * 2 F 14e Page S43

44 * 2 Me 14f * 2 Me 14f Page S44

45 * 2 Me 14g Page S45

46 * 2 Me 14g * Cl 14h 2 Page S46

47 * Cl 14h 2 Page S47

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