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Enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers using a cross-metathesis allylboration sequence

Academic Article
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Overview

related to degree

  • Winbush, SusAnn, Ph.D. in Chemistry, Scripps Research 2005 - 2010

authors

  • Winbush, SusAnn
  • Roush, William

publication date

  • October 2010

journal

  • Organic Letters  Journal

abstract

  • The enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers via a two-step sequence involving olefin cross-metathesis of ?-alkoxyallylboronate 4 and subsequent allylboration of the derived bisboryl intermediate 6 provides triol monoethers 7 with good to excellent diastereoselectivity.
  • The enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers via a two-step sequence involving olefin cross-metathesis of β-alkoxyallylboronate 4 and subsequent allylboration of the derived bisboryl intermediate 6 provides triol monoethers 7 with good to excellent diastereoselectivity.

subject areas

  • Boron Compounds
  • Ethers
  • Molecular Structure
  • Silanes
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2945398

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol101789g

PubMed ID

  • 20806914
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Additional Document Info

start page

  • 4344

end page

  • 4347

volume

  • 12

issue

  • 19

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