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Stereloselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols

Academic Article
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Overview

authors

  • Li, F. Z.
  • Roush, William

publication date

  • July 2009

journal

  • Organic Letters  Journal

abstract

  • A stereoselective method for synthesis of syn,syn- and syn,anti-1,3,5-triols based on a double allylboration-intramolecular hydrosilylation sequence has been developed. The 1,3-syn stereocontrol is achieved in the intramolecular hydrosilylation of monoprotected (Z)-1,5-syn-diols and (E)-1,5-anti-diols with 87:13 to 95:5 and 86:14 to 88:12 diastereomeric ratios, respectively, by using 0.5 mol % of Karstedt's catalyst in toluene.

subject areas

  • Alcohols
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Silanes
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2755244

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol9009877

PubMed ID

  • 19507846
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Additional Document Info

start page

  • 2932

end page

  • 2935

volume

  • 11

issue

  • 13

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