Chirale Ionische Flüssigkeiten in der homogenen Katalyse

Experimenteller Teil
L-Prolin-methylester-bis[(trifluoromethyl)sulfonyl]amid 12a
Ausbeute: 76.3 % (6.3 g, 15.3 mmol)
NH +
H
O
O Me
12a
122
NTf 2 -
C8H12F6N2O6S2, 410.31 g/mol
1 H-NMR (300 MHz, [D6]-DMSO): = 1.92 (q, J = 6.3 Hz, 2H, NCH2CH2), 2.08-2.09 (m, 1H, CHCH2),
2.28 (d, J = 6.3 Hz, 1H, CHCH2), 3.23 (q, J = 7.4Hz, 2H, NCH2), 3.78 (s, 3H, OCH3), 4.37-4.44 (d, J =
7.4 Hz, 1H, NCH), 9.12 (s (br), 2H, NH2) ppm.
13 C-NMR (75.5 MHz, [D6]-DMSO): = 22.9 (NCH2CH2), 27.6 (CHCH2), 45.6 (NCH2), 52.9 (OCH3),
58.6 (NCH), 119.5 (q, J = 321.8 Hz, CF3), 169.3 (COO) ppm.
Wassergehalt (Karl-Fischer): 40 ppm
TG: 74.1 °C (onset: 27.5 °C)
20
Drehwert (DCM): []D = -16.5 °
Viskosität: 4.6*10 3 Pas (20°C)
N-Methyl-L-Prolin-methylester-bis[(trifluoromethyl)sulfonyl]amid 11b
Ausbeute: 78.2 % (6.6 g, 15.6 mmol)
NH +
Me
O
O
Me
12b
NTf 2 -
C9H14F6N2O6S2, 424.02 g/mol
1 H-NMR (300 MHz, [D6]-DMSO): = 1.85-1.99 (m, 1H, CH2), 2.00-2.16 (m, 2H, CH2), 2.39-2.49 (m,
1H, CH2), 2.91 (s, 3H, NCH3), 3.09-3.30 (m, 1H, NCH2), 3.54-3.67 (m, 1H, NCH2), 3.80 (s, 3H, OCH3),
4.30-4.44 (m, 1H, CH), 10.01 (s (br), 1H, NH) ppm.
13 C-NMR (75.5 MHz, [D6]-DMSO): = 21.66 (NCH2CH2), 27.35 (CHCH2), 40.08 (NCH3), 52.82
(OCH3), 56.13 (CH2), 66.68 (CH), 119.4 (q, J = 321.7 Hz, CF3), 168.54 (COO) ppm.
Wassergehalt (Karl-Fischer): 40 ppm
20
Drehwert (DCM): []D = -24.2 °