Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 21, Pages 4241-4245Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800914
Keywords
Cu(II) catalysis; Enol esters; Chan Lam Evans reaction; Activated esters; Boroxines
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Funding
- Netherlands Organization for Scientific Research (NWO-CW) [711.014.010]
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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.
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