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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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Overview

related to degree

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

authors

  • Hicks, J. D.
  • Huh, Chan-Woo
  • Legg, A. D.
  • Roush, William

publication date

  • December 2007

journal

  • Organic Letters  Journal

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.

subject areas

  • Ethers
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Identity

PubMed Central ID

  • PMC2504016

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol702588h

PubMed ID

  • 18027963
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Additional Document Info

start page

  • 5621

end page

  • 5624

volume

  • 9

issue

  • 26

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