title: Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.
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.
authors.affiliation: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
authors.forename: Jacqueline D
authors.initials: JD
authors.lastname: Hicks
authors.forename: Chan Woo
authors.initials: CW
authors.lastname: Huh
authors.forename: Ashley D
authors.initials: AD
authors.lastname: Legg
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D004987:Ethers / Q000737:chemistry*
chemical_list: D004987:Ethers