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Variation of Silyl Chloride
 | ||||
|---|---|---|---|---|
| silyl chloridea |
bis-silyl | mono-silyl 9a-e |
allylic: homoallylic |
recov. SM |
| TMS | 27% | 26% | 78:22 | 19% |
| TESCl | 16% | 59% | 89:11 | 14% |
| TBSCl | 8% | 55% | 89:11 | 33% |
| TBDPSCl | 12% | 53% | 92:8 | 33% |
| TIPS | 5% | 54% | 94:6 | 27% |
Reactions were performed by treating a solution of the 1,5-diol (1 equiv), imidazole (1.15 equiv), and DMAP (0.05 equiv) in CH2Cl2-DMF (1:1, 0.1 M) at room temperature with silyl chloride (1.1 equiv)
