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Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane

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

  • April 2013

journal

  • Organic Letters  Journal

abstract

  • The enantioselective hydroboration of racemic allenylsilane (±)-4 with ((d)Ipc)2BH proceeds via enantiodivergent pathways to give vinylborane 11 and crotylborane intermediate (S)-E-5. Subsequent crotylboration of aldehyde substrates with (S)-E-5 at -78 °C provides (E)-δ-silyl-anti-homoallylic alcohols in 71-89% yield and with 93-96% ee.

subject areas

  • Alcohols
  • Aldehydes
  • Alkadienes
  • Boron Compounds
  • Molecular Structure
  • Silanes
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC3663895

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol4004405

PubMed ID

  • 23534391
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Additional Document Info

start page

  • 1662

end page

  • 1665

volume

  • 15

issue

  • 7

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