Table 4.
entry | allenamides | conditions (time) | amido-alkenes | yield [%]b,c | ||
1 | 29a: R = Ph | 115 °C (16 h) | 33a | 71 | ||
2 | 29b: R = H | —d | 33b | 90 | ||
3 | 30 | 115 °C (16 h) | 34 | 79 | ||
4 | 31a: R = H | CSA (10 min) | 35a | 68 | ||
5 | 31b: R = Me | CSA (10 min) | 35b | 80 | ||
6 | 32 | CSA (10 min) | 36 | 84 |
aUnless otherwise noted, CH3CN was the solvent for thermal conditions and CH2Cl2 was the solvent when using 10 mol % of CSA at rt. For all reactions, concn = 0.10 M. bAll were isolated yields. cAll amido-di- and trienes were exclusively E-selective [≥95:5]. dSee text for this isomerization.