Table 1 Reaction development and the control experimenta
Entry | Derivation from standard condition | Yields of 3a (%) | Yields of recovered donor (%) | Yields of 4 (%) |
---|---|---|---|---|
1 | None | 96 | - | 99 |
2 | No Sc(OTf)3 | 0 | >95 | 0 |
3 | Bi(OTf)3 as the catalyst | 65 | 40 | 58 |
4 | Zn(OTf)2 or Ca(OTf)2/nBu4NPF6 or B(C6F5)3 as catalyst | 0 | >95 | 0 |
5 | TfOH as catayst | complex mixture | - | NA |
6 | TMSOTf as catalyst | <5 | >95 | <5 |
7 | Ph3PAuNTf2 as catalyst | 0 | >95 | 0 |
8 | 4 Å MS instead of 5 Å MS | 33 | 68 | 30 |
9 | CH2Cl2 as the solvent | 99 | - | 99 |
10 | PhCH3 or PhCF3 or Et2O as solvent | 96–97 | - | >95 |
11b | glucose pentabenzoate 5 as donor | trace | >95 | NA |