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Enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols via aldehyde allylboration using alpha-stannylallylboranes generated by allene hydroboration followed by a highly diastereoselective 1,3-boratropic shift

Academic Article
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Overview

related to degree

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

authors

  • Chen, Ming
  • Ess, D. H.
  • Roush, William

publication date

  • June 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A highly enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols 4 via aldehyde allylboration reactions of the double-chiral allylborane reagent 2a is reported. Allylborane 2a was generated from the hydroboration of commercially available allenylstannane 1 with ((d)Ipc)(2)BH at -40 to -20 degrees C followed by a kinetically controlled and highly diastereoselective 1,3-boratropic shift in intermediate 3a.

subject areas

  • Aldehydes
  • Alkadienes
  • Boranes
  • Membrane Glycoproteins
  • Models, Molecular
  • Molecular Conformation
  • Propanols
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2890212

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja103041u

PubMed ID

  • 20496899
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Additional Document Info

start page

  • 7881

end page

  • 7883

volume

  • 132

issue

  • 23

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