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Thermodynamic control of 1,3-boratropic shifts of α- and γ-stannyl-substituted allylboranes: hyperconjugation outweighs steric effects

Academic Article
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Overview

related to degree

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

authors

  • Stewart, P. S.
  • Chen, Ming
  • Roush, William
  • Ess, D. H.

publication date

  • 2011

journal

  • Organic Letters  Journal

abstract

  • (E)-δ-Stannyl homoallylic alcohols are prepared by an allene hydroboration-aldehyde allylboration sequence ( Chen , M. et al. J. Am. Chem. Soc. 2010 , 132, 7881 ). Key to this reaction sequence is that the kinetic allene hydroboration product, 2a, is less stable than and isomerizes to the more sterically congested α-stannylallylborane 3a (see abstract figure). An M06-2X density functional analysis shows that the C-Sn to boron σ-π hyperconjugation interaction is sufficiently stabilizing to override the steric congestion in 3a.

subject areas

  • Alcohols
  • Aldehydes
  • Alkadienes
  • Boranes
  • Organotin Compounds
  • Stereoisomerism
  • Thermodynamics
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Identity

PubMed Central ID

  • PMC3462665

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol2001599

PubMed ID

  • 21323387
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Additional Document Info

start page

  • 1478

end page

  • 1481

volume

  • 13

issue

  • 6

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