supplementary material dianhydrohexitols: new tools for
TRANSCRIPT
![Page 1: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/1.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S1 ©ARKAT-USA, Inc.
Supplementary Material
Dianhydrohexitols: new tools for organocatalysis. Application in
enantioselective Friedel-Crafts alkylation of indoles with
nitroalkenes
Ling-Yan Chen,a,b Stéphane Guillarme,aand Christine Saluzzoa*
a IMMM, MSO, UMR CNRS 6283, Faculté des Sciences, Université du Maine,
Av. O. Messiaen, 72085 Le Mans Cedex 09, France b College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science,
201620, China
E-mail: [email protected]
Table of contents
NMR data 1H NMR spectrum of compound 7: S3 13C NMR spectrum of compound 7: S4 1H NMR spectrum of compound 8: S5 13C NMR spectrum of compound 8: S6 1H NMR spectrum of compound 9: S7 13C NMR spectrum of compound 9: S8 1H NMR spectrum of compound 10: S9 13C NMR spectrum of compound 10: S10 1H NMR spectrum of compound 6: S11 13C NMR spectrum of compound 6: S12 1H NMR spectrum of compound 1: S13 13C NMR spectrum of compound 1: S14 1H NMR spectrum of compound 2: S14 13C NMR spectrum of compound 2: S15 1H NMR spectrum of compound 3: S16 13C NMR spectrum of compound 3: S17 1H NMR spectrum of compound 4: S18 13C NMR spectrum of compound 4: S19 1H NMR spectrum of compound 5: S20 13C NMR spectrum of compound 5: S21 1H NMR spectrum of compound 14a: S22 13C NMR spectrum of compound 14a: S23
![Page 2: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/2.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S2 ©ARKAT-USA, Inc.
1H NMR spectrum of compound 14b: S24 13C NMR spectrum of compound 14b: S25 1H NMR spectrum of compound 14c: S26 13C NMR spectrum of compound 14c: S27 1H NMR spectrum of compound 14d: S28 13C NMR spectrum of compound 14d: S29 1H NMR spectrum of compound 14e: S30 13C NMR spectrum of compound 14e: S31 1H NMR spectrum of compound 14f: S32 13C NMR spectrum of compound 14f: S33 1H NMR spectrum of compound 14g: S34 13C NMR spectrum of compound 14g: S35 1H NMR spectrum of compound 14h: S36 13C NMR spectrum of compound 14h: S37
Catalytic enantioselective Friedel-Crafts alkylation in the presence of thiourea catalyst 2:
HPLC 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 3: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/3.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S3 ©ARKAT-USA, Inc.
NMR Spectra
OTs
TsO
![Page 4: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/4.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S4 ©ARKAT-USA, Inc.
OTs
TsO
![Page 5: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/5.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S5 ©ARKAT-USA, Inc.
N3
N3
![Page 6: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/6.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S6 ©ARKAT-USA, Inc.
N3
N3
![Page 7: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/7.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S7 ©ARKAT-USA, Inc.
O O
NH2
H2N
![Page 8: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/8.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S8 ©ARKAT-USA, Inc.
O O
NH2
H2N
![Page 9: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/9.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S9 ©ARKAT-USA, Inc.
N3
N3
![Page 10: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/10.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S10 ©ARKAT-USA, Inc.
N3
N3
![Page 11: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/11.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S11 ©ARKAT-USA, Inc.
O
OHN
NH
NH
S
CF3
CF3
HN
S
F3C
F3C
![Page 12: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/12.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S12 ©ARKAT-USA, Inc.
O
OHN
NH
NH
S
CF3
CF3
HN
S
F3C
F3C
![Page 13: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/13.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S13 ©ARKAT-USA, Inc.
O
OH2N
NH N
H
S
CF3
CF3
![Page 14: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/14.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S14 ©ARKAT-USA, Inc.
O
OHN
NH
NH
S
CF3
CF3
HN
S
F3C
F3C
O
OH2N
NH N
H
S
CF3
CF3
![Page 15: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/15.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S15 ©ARKAT-USA, Inc.
O
OHN
NH
NH
S
CF3
CF3
HN
S
F3C
F3C
![Page 16: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/16.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S16 ©ARKAT-USA, Inc.
O
OHN
NH
NH
SHN
S
![Page 17: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/17.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S17 ©ARKAT-USA, Inc.
O
OHN
NH
NH
SHN
S
![Page 18: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/18.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S18 ©ARKAT-USA, Inc.
O
OHN
NH
NH
SHN
S
![Page 19: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/19.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S19 ©ARKAT-USA, Inc.
O
OHN
NH
NH
SHN
S
![Page 20: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/20.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S20 ©ARKAT-USA, Inc.
O
OHN
NH N
H
S
CF3
CF3
SO2
O
![Page 21: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/21.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S21 ©ARKAT-USA, Inc.
O
OHN
NH N
H
S
CF3
CF3
SO2
O
![Page 22: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/22.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S22 ©ARKAT-USA, Inc.
![Page 23: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/23.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S23 ©ARKAT-USA, Inc.
![Page 24: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/24.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S24 ©ARKAT-USA, Inc.
![Page 25: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/25.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S25 ©ARKAT-USA, Inc.
![Page 26: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/26.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S26 ©ARKAT-USA, Inc.
![Page 27: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/27.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S27 ©ARKAT-USA, Inc.
![Page 28: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/28.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S28 ©ARKAT-USA, Inc.
![Page 29: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/29.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S29 ©ARKAT-USA, Inc.
![Page 30: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/30.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S30 ©ARKAT-USA, Inc.
![Page 31: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/31.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S31 ©ARKAT-USA, Inc.
![Page 32: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/32.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S32 ©ARKAT-USA, Inc.
![Page 33: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/33.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S33 ©ARKAT-USA, Inc.
![Page 34: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/34.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S34 ©ARKAT-USA, Inc.
![Page 35: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/35.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S35 ©ARKAT-USA, Inc.
![Page 36: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/36.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S36 ©ARKAT-USA, Inc.
![Page 37: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/37.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S37 ©ARKAT-USA, Inc.
![Page 38: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/38.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S38 ©ARKAT-USA, Inc.
HPLC Data
PhNO2
NH
*
14a
![Page 39: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/39.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S39 ©ARKAT-USA, Inc.
PhNO2
NH
*
14a
NO2
NHMeO
*
14b
![Page 40: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/40.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S40 ©ARKAT-USA, Inc.
NO2
NHMeO
*
14b
NO2
NHBr
*
14c
![Page 41: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/41.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S41 ©ARKAT-USA, Inc.
NO2
NHBr
*
14c
NO2
NH
Cl
*
14d
![Page 42: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/42.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S42 ©ARKAT-USA, Inc.
NO2
NH
Cl
*
14d
![Page 43: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/43.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S43 ©ARKAT-USA, Inc.
NO2
NH
F
*
14e
NO2
NH
F
*
14e
![Page 44: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/44.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S44 ©ARKAT-USA, Inc.
NO2
NH
Me
*
14f
NO2
NH
Me
*
14f
![Page 45: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/45.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S45 ©ARKAT-USA, Inc.
NO2
NH
MeO
*
14g
![Page 46: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/46.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S46 ©ARKAT-USA, Inc.
NO2
NH
MeO
*
14g
NO2
NH
Cl
*
14h
![Page 47: Supplementary Material Dianhydrohexitols: new tools for](https://reader030.vdocuments.us/reader030/viewer/2022012409/616a443311a7b741a350a1c9/html5/thumbnails/47.jpg)
General Papers ARKIVOC 2013 (iii) S1-S47
Page S47 ©ARKAT-USA, Inc.
NO2
NH
Cl
*
14h