Table 3.
Influence of temperature on the Diels-Alder reaction.
entrya | reaction temperature [°C] | reaction time [h] | yield [%]b | ee [%]c |
1 | 23 | 1 | 84 | 30 |
2 | 0 | 24 | 96 | 29 |
3 | −20 | 24 | 98 | 31 |
4 | −40 | 48 | 96 | 36 |
5 | −70 | 96 | 71 | 39 |
aAll reactions were carried out using 0.1 mmol maleimide 2a, 1.1 equiv anthrone (1a) and 0.1 (entry 1–4) or 0.25 equiv (entry 5) of 8c in 1 mL abs. dichloromethane. bIsolated yield after column chromatography. cEnantiomeric excess was determined by HPLC using Chiralpak IA column.