851348-76-0Relevant academic research and scientific papers
Efficient and scalable protocol for the Z-selective synthesis of unsaturated esters by horner-wadsworth-emmons olefination
Touchard, Francois P.,Capelle, Nicolas,Mercier, Mathilde
, p. 707 - 711 (2005)
The synthesis of a highly Z-selective Horner-Wadsworth-Emmons (HWE) reagent from cheap and readily available starting materials on a 200-g scale is described. The HWE reaction conditions have also been studied in order to design an efficient and scalable
The stereochemical course of intramolecular michael reactions
Kwan, Eugene E.,Scheerer, Onathan R.,Evans, David A.
, p. 175 - 203 (2013/04/10)
We present a general model for understanding the stereochemical course of intramolecular Michael reactions. We show that the addition of β- ketoester enolates to α,β-unsaturated esters and imides bearing adjacent stereocenters (X, Y = H, Me, OR) leads to high levels of asymmetric induction. Reinforcing and nonreinforcing stereochemical relationships are evaluated from the syn and anti reactant diastereomers. On the basis of synthetic, spectroscopic, and computational studies, we propose that the outcomes of these reactions can be rationalized by a dipole-minimized chair transition-state model.
Exploiting domino enyne metathesis mechanisms for skeletal diversity generation
Spandl, Richard J.,Rudyk, Helene,Spring, David R.
supporting information; experimental part, p. 3001 - 3003 (2009/02/04)
In the context of diversity-oriented synthesis, the exploration and optimization of the domino metathesis of decorated norbornenes allowed complex polycyclic architectures to be generated in a highly efficient and atom-economical process. The Royal Society of Chemistry.
Phosphonate modification for a highly (Z)-selective synthesis of unsaturated esters by Horner-Wadsworth-Emmons olefination
Touchard, Francois P.
, p. 1790 - 1794 (2007/10/03)
The Horner-Wadsworth-Emmons (HWE) reaction of various ethyl diarylphosphonoacetates with benzaldehyde, cyclohexane carboxaldehyde and octanal is reported. Selectivities of up to 98% at -78°C are obtained with the three substrates. Among all the phosphonates prepared, the reagent based on 2-tert-butylphenol proved to be especially efficient, with Z/E ratios close to 95:5 at 0°C. It appears thus to be the reagent of choice for the (Z)-selective HWE reaction with both aromatic and aliphatic aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
