Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).
Steemers, Luuk,Wijsman, Linda,van Maarseveen, Jan H.
supporting information
p. 4241 - 4245
(2018/10/02)
VINYL ESTER PRODUCTION FROM ACETYLENE AND CARBOXYLIC UTILIZING HOMOGENEOUS CATALYST
A process for the selective production of vinyl ester by the reaction of a carboxylic acid with acetylene with a homogeneous catalyst is disclosed and claimed. In a preferred embodiment of this invention, reaction of benzoic acid and acetylene in the presence of Group VIII metal complex catalyst at a temperature of about 50 to 1800C results in quantitative yields of vinyl benzoate.
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Page/Page column 73-74
(2010/11/18)
A new methodology for the preparation of vinyl esters
A new methodology has been developed for the preparation of unsubstituted enol esters. Its application is demonstrated by the obtainment of vinyl aromatic α-amino esters. A brief investigation of the preparation of other hydrophobic vinyl esters proved successful. Because of the mild reaction conditions employed, it is believed this route should provide access to other enol esters.