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Switch in regioselectivity of epoxide ring-opening by changing the organometallic reagent José A. Gálvez,a* María D. Díaz de Villegas,a* Ramón Badorrey,a and Pilar López-Ram-de-Víua a Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain. Fax: +34976761202; Tel: +34976762274; E-mail: [email protected]. Table of contents 1H NMR and 13C NMR spectra for compound syn-2b 2 1H NMR and 13C NMR spectra for compound anti-2b 3 1H NMR and 13C NMR spectra for compound 3 4 1H NMR and 13C NMR spectra for compound 4 5 1H NMR and 13C NMR spectra for compound 5 6 1H NMR and 13C NMR spectra for compound 6 7 1H NMR and 13C NMR spectra for compound 7a 8 1H NMR and 13C NMR spectra for compound 7b 9 1H NMR and 13C NMR spectra for compound 7b 10 1H NMR and 13C NMR spectra for compound 8a 11 1H NMR and 13C NMR spectra for compound 8b 12 1H NMR and 13C NMR spectra for compound 8d 13 1H NMR and 13C NMR spectra for compound 8e 14 1H NMR and 13C NMR spectra for compound 9a 15 1H NMR and 13C NMR spectra for compound 9b 16 1H NMR and 13C NMR spectra for compound 9d 17 1H NMR and 13C NMR spectra for compound 9e 18 1H NMR and 13C NMR spectra for compound 10 19
ORTEP drawing of compound 9e 20
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
2
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
OO
HN
syn-2b
Ph
Me
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
3
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
OO
HN
ant i-2b
Ph
Me
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
4
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
OO
N Ph
Me
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
5
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
OO
N Ph
Me
4
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
6
ppm (t1)1.02.03.04.05.06.07.0
AcOEt
AcOEt
AcOEt
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
OH
N Ph
Me
5
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
7
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
6
O
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
8
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
7aMe
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
9
ppm (f1)1.02.03.04.05.06.07.0
dichloromethane
1H NMR 400 MHz, rt, CDCl3
ppm (f1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
7bPh
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
10
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
7c
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
11
ppm (f1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (f1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
8aOH
Me
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
12
ppm (t1)1.02.03.04.05.06.07.0
dichloromethane
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
8bOH
Ph
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
13
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
8dOH
i-Pr
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
14
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
N Ph
Me
8eOH
Bn
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
15
ppm (t1)1.02.03.04.05.06.07.0
grease
greas
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
grease
13C NMR 100 MHz, rt, CDCl3
NH
9a
OH
Me
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
16
ppm (t1)1.02.03.04.05.06.07.0
grease
greaseEtOH
EtOH
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
grease
13C NMR 100 MHz, rt, CDCl3
NH
9b
OH
Ph
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
17
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
NH
9d
OH
i -Pr
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
18
ppm (t1)1.02.03.04.05.06.07.0
dichloromethane
1H NMR 400 MHz, rt, CDCl3
ppm (t1)50100150
13C NMR 100 MHz, rt, CDCl3
NH
9e
OH
Bn
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
19
ppm (t1)1.02.03.04.05.06.07.0
1H NMR 300 MHz, 333 K, CDCl3
ppm (t1)50100150
13C NMR 75 MHz, 333K, CDCl3
N
10
Ph
OH
Boc
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
20
ORTEP drawing of compound 9e. Thermal ellipsoids are at 50% probability level.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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