Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers

Academic Article
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related to degree

  • Huh, Chan-Woo, Ph.D. in Organic Chemistry, Scripps Research , transferred from University of Michigan with advisor 2005 - 2008

publication date

  • 2007

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.