Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
This journal is © The Royal Society of Chemistry 2016
Supplementary Information
Lewis acid catalyzed 3+2] annulation of ketenimines with donor-acceptor
cyclopropanes: an approach to 2-alkylydenepyrrolidine derivatives
Mateo Alajarin, Adrian Egea, Raul-Angel Orenes and Angel Vidal
Figure S1 Dimer of 3a due to the formation of two CH/pi hydrogen bonds
Figure S2 Showing two neighboring dimers packing in the crystal of 3a
Figure S3 Torsion angle between the pyrrolidine and cyclohexane rings in compound
8b
Figure S4 Formation of infinite chains by hydrogen bonds along the a-axis in the
crystal of 8b
Figure S5 Formation of infinite chains by hydrogen bonds along the c-axis in the
crystal of 8b
Figure S6 Formation of infinite chains along the a-axis (red) and the c-axis (orange)
and the interconnection of the chain (Green) froming layers in the ac-plane of the
cristal of 8b (some molecules have been omitted for clarity)
CO2CH3
CO2CH3
Ph
N
Ph
1H
NMR of 3a (300 MHz)
CH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3a (75 MHz)
CH3
CO2CH3
CO2CH3
Ph
N
1H
Ph
NMR of 3b (300 MHz)
OCH3
CO2CH3
CO2CH3
Ph
N
13C
Ph
NMR of 3b (75 MHz)
OCH3
CO2CH3
CO2CH3
CH3O
1H
NMR of 3c (400 MHz)
Ph
N
Ph
CH3O
OCH3
CH3
CO2CH3
CO2CH3
CH3O
13C
NMR of 3c (100 MHz)
Ph
N
Ph
CH3O
OCH3
CH3
CO2CH3
CO2CH3
CH3O
1H
NMR of 3d (300 MHz)
Ph
N
Ph
CH3O
OCH3
OCH3
CO2CH3
CO2CH3
CH3O
13C
NMR of 3d (75 MHz)
Ph
N
Ph
CH3O
OCH3
OCH3
CO2CH3
CO2CH3
CH3O
1H
NMR of 3e (400 MHz)
N
CO2Et
CH3
CH3O
OCH3
CH3
CO2CH3
CO2CH3
CH3O
13C
NMR of 3e (100 MHz)
N
CO2Et
CH3
CH3O
OCH3
CH3
CO2CH3
CO2CH3
CH3O
NOESY of 3e
N
CO2Et
CH3
CH3O
OCH3
CH3
CO2CH3
CO2CH3
OCH3
CH3O
1H
NMR of 3f (300 MHz)
Ph
N
Ph
CH3O
CH3
CO2CH3
CO2CH3
OCH3
CH3O
13C
NMR of 3f (75 MHz)
Ph
N
Ph
CH3O
CH3
CO2CH3
CO2CH3
Ph
N
1H
Ph
NMR of 3g (400 MHz)
CH3
CO2CH3
CO2CH3
Ph
N
13C
Ph
NMR of 3g (100 MHz)
CH3
CO2CH3
CO2CH3
Ph
N
1H
Ph
NMR of 3h (400 MHz)
OCH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3h (100 MHz)
OCH3
CO2CH3
CO2CH3
Ph
N
Ph
1H
NMR of 3i (400 MHz)
CH3
CO2CH3
CO2CH3
Ph
N
13C
Ph
NMR of 3i (100 MHz)
CH3
CO2CH3
CO2CH3
Ph
N
1H
Ph
NMR of 3j (400 MHz)
OCH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3j (100 MHz)
OCH3
CO2CH3
CO2CH3
Ph
N
1H
NMR of 3k (400 MHz)
Ph
OCH3
CO2CH3
CO2CH3
Ph
N
13C
NMR of 3k (100 MHz)
Ph
OCH3
CO2CH3
CO2CH3
Ph
N
1H
Ph
NMR of 3l (400 MHz)
CH3O
CH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3l (100 MHz)
CH3O
CH3
CO2CH3
CO2CH3
Ph
N
Ph
1H
NMR of 3m (400 MHz)
CH3O
OCH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3m (100 MHz)
CH3O
OCH3
CO2CH3
CO2CH3
Ph
N
1H
NMR of 3n (400 MHz)
Ph
CH3O
OCH3
CO2CH3
CO2CH3
Ph
N
13C
NMR of 3n (100 MHz)
Ph
CH3O
OCH3
CO2CH3
CO2CH3
Ph
N
1H
Ph
NMR of 3o (400 MHz)
CH3
CH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3o (100 MHz)
CH3
CH3
CO2CH3
CO2CH3
Ph
N
Ph
1H
NMR of 3p (400 MHz)
CH3
OCH3
CO2CH3
CO2CH3
Ph
N
Ph
13C
NMR of 3p (100 MHz)
CH3
OCH3
CH3
Ph
Ph
1H
NMR of 8a (400 MHz)
H
N
CO2CH3
H
CO2CH3
CH3
Ph
Ph
13C
NMR of 8a (100 MHz)
H
N
CO2CH3
H
CO2CH3
OCH3
Ph
CH3O
Ph
1H
NMR of 8b (400 MHz)
H
N
CO2CH3
H
CO2CH3
OCH3
Ph
CH3O
Ph
13C
NMR of 8b (100 MHz)
H
N
CO2CH3
H
CO2CH3
CH3
Ph
Ph
1H
NMR of 10a (400 MHz)
CH3O
H
N
CO2CH3
H
CH3O
O
CO2CH3
CH3
Ph
Ph
13C
NMR of 10a (100 MHz)
CH3O
H
N
CO2CH3
H
CH3O
O
CO2CH3
CH3O
Ph
Ph
1H
NMR of 10b (400 MHz)
CH3O
H
N
CO2CH3
H
CH3O
O
CO2CH3
CH3O
Ph
Ph
13C
NMR of 10b (100 MHz)
CH3O
H
N
CO2CH3
H
CH3O
O
CO2CH3
CO2CH3
CO2CH3
1H
NMR of 14 (300 MHz)
Ph
N
Ph
CO2CH3
CO2CH3
13C
NMR of 14 (75 MHz)
Ph
N
Ph