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