Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers |
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| Authors: | Hicks Jacqueline D Huh Chan Woo Legg Ashley D Roush William R |
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| Affiliation: | Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA. |
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| Abstract: | Treatment of unsaturated 1,5-diols 2 with TES-Cl (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with >95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments. |
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