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Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions

Academic Article
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Overview

related to degree

  • Chen, Ming, Ph.D. in Organic Chemistry, Scripps Research 2007 - 2012

authors

  • Chen, Ming
  • Roush, William

publication date

  • 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Chiral Brønsted acid catalyzed asymmetric allenylboration reactions are described. Under optimized conditions, anti-homopropargyl alcohols 2 are obtained in high yields with excellent diastereo- and enantioselectivities from stereochemically matched aldehyde allenylboration reactions with (M)-1 catalyzed by the chiral phosphoric acid (S)-4. The syn-isomers 3 can also be obtained in good diastereoselectivities and excellent enantioselectivities from the mismatched allenylboration reactions of aromatic aldehydes using (M)-1 in the presence of the enantiomeric phosphoric acid (R)-4. The stereochemistry of the methyl group introduced into 2 and 3 is controlled by the chirality of the allenylboronate (M)-1, whereas the configuration of the new hydroxyl stereocenter is controlled by the enantioselectivity of the chiral phosphoric acid catalyst used in these reactions. The synthetic utility of this methodology was further demonstrated in highly diastereoselective syntheses of a variety of anti, anti-stereotriads, the direct synthesis of which has constituted a significant challenge using previous generations of aldol and crotylmetal reagents.

subject areas

  • Aldehydes
  • Alkadienes
  • Alkynes
  • Boronic Acids
  • Catalysis
  • Organophosphates
  • Propanols
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Identity

PubMed Central ID

  • PMC3474359

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja3031467

PubMed ID

  • 22731887
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Additional Document Info

start page

  • 10947

end page

  • 10952

volume

  • 134

issue

  • 26

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