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Concerning the application of the 1H NMR ABX analysis for assignment of stereochemistry to aldols deriving from aldehydes lacking beta-branches

Academic Article
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Overview

authors

  • Dias, L. C.
  • Aguilar, A. M.
  • Salles, A. G.
  • Steil, L. J.
  • Roush, William

publication date

  • 2005

journal

  • Journal of Organic Chemistry  Journal

abstract

  • [reactions: see text] Attempts to apply the 1H NMR ABX method for assignment of stereochemistry of beta-hydroxy ketones to aldols 4-10 deriving from alpha-methyl aldehydes lacking beta-branches reveals that the presence of a beta-branch in the aldehyde reaction partner is necessary so that the average chemical environment of Ha and Hb is different for the Felkin and anti-Felkin aldols (see conformational pairs A/B and C/D, respectively). When the chiral alpha-methyl aldehyde lacks a beta-branch, as in the case of the aldehyde precursors to 4-10, the conformational energies of E and F (for the Felkin beta-hydroxy ketone derivatives), and conformers G and H for the anti-Felkin aldols, are too close in energy (within each pair), such that the average chemical and magnetic environments of Ha and Hb in the two diastereomers cannot be easily distinguished. This analysis provides a rational basis for application of the 1H NMR ABX pattern analysis to other beta-hydroxy ketone derivatives.

subject areas

  • Aldehydes
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo051773e

PubMed ID

  • 16323858
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Additional Document Info

start page

  • 10461

end page

  • 10465

volume

  • 70

issue

  • 25

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