Table 1.
Reaction development and the control experimenta
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|---|---|---|---|---|
| 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 |
aUnless otherwise specified, all reactions were performed with 1.2 equiv of 1a, 1.0 equiv of 2a (0.05 mmol) in the presence of the catalyst (0.1 equiv) and 5 Å MS in corresponding solvent (0.05 M, 1 mL) for 2–5 h at room temperature. The yield for 3a was based on 2a, and the yields for 4 and the recovered donor were based on the 1a. bCH2Cl2 was used as the solvent. Bz Benzoyl, Me Methyl, Tf Trifluoromethanesulfonyl, DCE 1,2-dichloroethane, nBu n-Butyl, TMS Trimethylsilyl, Ph Phenyl, MS Molecular sieve, Et Ethyl, NA Not applicable.
