Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/56460
Type: Artigo de periódico
Title: Concerning the application of the H-1 NMR ABX analysis for assignment of stereochemistry to aldols deriving from aldehydes lacking beta-branches
Author: Dias, LC
Aguilar, AM
Salles, AG
Steil, LJ
Roush, WR
Abstract: Attempts to apply the H-1 NMR ABX method for assignment of stereochemistry of beta-hydroxy ketones to aldols 4-10 deriving from a-methyl aldehydes lacking P-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 P-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 H-1 NMR ABX pattern analysis to other beta-hydroxy ketone derivatives.
Country: EUA
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/jo051773e
Date Issue: 2005
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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