The mechanism of ynol ether formation from dichloroenol ethers, a decades-old transformation, has been studied by experimental and theoretical techniques to determine the relative importance of the Fritsch-Buttenberg-Wichell rearrangement (alpha-elimination) and beta-elimination in the evolution of the intermediate carbenoid.
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http://dx.doi.org/10.1021/ol801704u | DOI Listing |
Org Biomol Chem
March 2014
Université Joseph Fourier, Département de Chimie Moléculaire (SERCO), UMR-5250 CNRS, ICMG FR-2607, BP 53, 38041, Grenoble Cedex 9, France.
The addition of dimethylaluminium alkoxyacetylides to Ellman's sulfinylimines is described. The reaction proceeds with excellent diastereoselectivity and high yield to produce oxygenated propargylamines in one step starting from simple dichloroenol ethers.
View Article and Find Full Text PDFOrg Lett
October 2008
Département de Chimie Moléculaire (SERCO), Université Joseph Fourier, UMR-5250, ICMG FR-2607, CNRS BP 53, 38041 Grenoble Cedex 9, France.
The mechanism of ynol ether formation from dichloroenol ethers, a decades-old transformation, has been studied by experimental and theoretical techniques to determine the relative importance of the Fritsch-Buttenberg-Wichell rearrangement (alpha-elimination) and beta-elimination in the evolution of the intermediate carbenoid.
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