TABLE 1.
| |||||
---|---|---|---|---|---|
entry | substrate | 2 | % yield of 2b | 3 | % yield of 3b |
1 | 1a | 85 | 95 | ||
2 | 1b | 72 | 90 | ||
3 | 1c | 88 | 92c | ||
4 | 1d | 75 | 96c | ||
5 | 1e | 84 | 90c | ||
6 | 1f | 65 | 98 | ||
7 | 1g | 68 | 69c | ||
8 | 1h | 79 | 79c | ||
9 | 1i | 80 | 82 | ||
10 | 1j | 76 | 31 | ||
11 | 1k | 97 | 89c |
Each reaction was performed at least twice. Conditions: 1 (1 equiv), DEA (1.1 equiv), ether, rt, ~30 minutes followed by 0.1M HCl (20 min).
Isolated yield.
Product was isolated as the pinacol ester.