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A three-component coupling strategy for tetrahydrofuran synthesis: application of the diisopropyl tartrate modified (E)-gamma-(dimethylphenylsilyl)allylboronate as an alpha,gamma-allyl dianion equivalent

Academic Article
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Overview

authors

  • Micalizio, Glenn
  • Roush, William

publication date

  • February 2000

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] A highly convergent three-component coupling strategy for the stereocontrolled synthesis of 2,3,5-trisubstituted tetrahydrofurans is described. After allylboration of the first aldehyde with 1, the chiral, nonracemic allylsilanes 2 are coupled with a second aldehyde or ketone with Lewis acid catalysis to give tetrahydrofurans 3 or 4 with excellent selectivity. The 2,5-stereochemistry is controlled by operating under nonchelate (e.g., 3) or chelate (e.g., 4) conditions.

subject areas

  • Allyl Compounds
  • Boronic Acids
  • Furans
  • Organosilicon Compounds
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol9913082

PubMed ID

  • 10814351
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Additional Document Info

start page

  • 461

end page

  • 464

volume

  • 2

issue

  • 4

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