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Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using alpha-alkoxypropargylstannanes

Academic Article
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Overview

authors

  • Savall, B. M.
  • Powell, N. A.
  • Roush, William

publication date

  • September 2001

journal

  • Organic Letters  Journal

abstract

  • Propargylic 1,2-anti-diol derivatives 2 and 10 are prepared in high yield and excellent diastereoselectivity by addition of alpha-alkoxypropargylstannanes 4a and 4b to aldehydes in the presence of BuSnCl(3). We also introduce the use of KF on Celite as a convenient and mild reagent for removal of the organotin waste products of these reactions. Reaction: see text.

subject areas

  • Aldehydes
  • Alkynes
  • Biological Factors
  • Propanols
  • Stereoisomerism
  • Tin Compounds
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol016536m

PubMed ID

  • 11554842
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Additional Document Info

start page

  • 3057

end page

  • 3060

volume

  • 3

issue

  • 19

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