Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 6, Pages 913-918Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700146
Keywords
amine-thiourea catalysts; asymmetric catalysis; electron-deficient compounds; epoxidation; glycidic esters; organocatalysis
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Funding
- MIUR
- POR Regione Campania FESR O.O. 2.1 (FarmaBioNet)
- Danish National Research Foundation [DNRF-93]
- University of Salerno
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A novel class of synthetically important glycidic esters has been obtained via an asymmetric epoxidation of trans-alpha-cyano-alpha, beta-unsaturated esters catalysed by a multifunctional Cinchona alkaloidderived thiourea/tert-butyl hydroperoxide (TBHP) system. The glycidic esters, isolated in excellent yield with complete trans-diastereocontrol and high enantioselectivity, proved to be versatile building blocks to access challenging small targets bearing a quaternary stereocenter.
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