Table 1. Evaluation of Reaction Conditionsa.
entry | THIQ (equiv) | catalyst | time (h) | yield (%) |
---|---|---|---|---|
1 | 2 | 48 | 50 | |
2 | 2 | PhCOOH | 7 | 95 |
3 | 2 | AcOH | 23 | 92 |
4 | 2 | 2-EHA | 21 | 91 |
5b | 2 | PhCOOH | 44 | 56 |
6 | 1.5 | PhCOOH | 12 | 93 |
7 | 1.2 | PhCOOH | 12 | 88 |
8c | 1.5 | PhCOOH | 15 | 95 |
Reactions were performed on a 0.2 mmol scale. All yields correspond to isolated yields. dr >25:1 in all cases.
Reaction was run at 50 °C and remained incomplete.
Without 4 Å MS.