Table 1. Results from the Nitro-Aldol Reaction Test of the Reaction between Cyclohexanone and p-Nitrobenzaldehyde.
| samples | entrya | catalyst (mol %) | cyclohexanone (equiv) | H2Ob (equiv) | conversionc (%) | anti/sync | eed (%) |
|---|---|---|---|---|---|---|---|
| PRW–NH-C16 | 1f | 5 | 12.0 | 2.0 | >99 | 93:7 | 89 |
| 2 | 5 | 12.0 | 2.0 | >99 | 93:7 | 89 | |
| 3 | 5 | 12.0 | 1.0 | >99 | 93:7 | 88 | |
| 4 | 5 | 15.0 | e | 62 | 85:15 | 68 | |
| PRW–O-C16 | 5g | 5 | 12.0 | 2.0 | >99 | 91:9 | 84 |
| 6g | 5 | 12.0 | 1.0 | >99 | 91:9 | 71 | |
| 7g | 5 | 15.0 | e | 94 | 86:14 | 73 |
a
The reactions were performed at room temperature, for 2 days, with vigorous stirring.
b
Water excess toward cyclohexanone (v/v).
c
The diastereomeric ratios and conversion were determine by 1H NMR analysis of the crude mixture.
d
Determined by chiral-phase HPLC analysis of the anti isomer.
e
Neat (no water addition).
f
HFIP was not used.
g
Results presented in ref (8).