Table 2. Reaction of Glycals 9a–d and 11a–c with Model Glycosyide Acceptors 2a, 2e, or 2g.
entry | R1 | R2 | R3 | product | time (h) | yield (%)a | α/βb | |
---|---|---|---|---|---|---|---|---|
1 | 9a | Bn | Bn | Bn | 10a | 1 | 88d,e | 21:1 |
2 | 9a | Bn | Bn | Bn | 10c | 1 | 94 | 26:1 |
3 | 9a | Bn | Bn | Bn | 10e | 2 | 84 | 30:1 |
4 | 9a | Bn | Bn | Bn | 10g | 7 | 62 | 25:1 |
5 | 9a | Bn | Bn | Bn | 10h | 7 | 68 | 20:1 |
6 | 9b | TBS | TBS | TBS | 11b | 1 | 92 | 30:1 |
7 | 9c | MOM | MOM | MOM | 11c | 1 | 71 | 20:1 |
8 | 9d | Si(tBu)2 | MOM | 11d | 1 | 82 | 20:1 | |
9 | 11a | Bn | Bn | Bn | 12ac | 17 | 54 | 30:1 |
10 | 11b | O[Si(i-Pr)2]2 | Bn | 12b | 17 | 78 | 30:1 | |
11 | 11c | O[Si(i-Pr)2]2 | TIPS | 12c | 17 | 75 | 30:1 | |
12 | 11c | O[Si(i-Pr)2]2 | TIPS | 13 | 17 | 86 | 30:1 | |
13 | 11c | O[Si(i-Pr)2]2 | TIPS | 14 | 17 | 64 | 20:1 |
Isolated yield.
Determined by 1H NMR.
10% Ferrier product 12a′ also isolated.
Reaction did not proceed in the absence of catalyst.
Reaction with BF3.OEt2 afforded 10a (<35%) and a mixture of products and starting material.