Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: use as catalysts in enantioselective asymmetric epoxidation.
journal contributionposted on 28.09.2015 by Philip C. Bulman Page, Christopher A. Pearce, Yohan Chan, Phillip Parker, Benjamin Buckley, Gerasimos A. Rassias, Mark Elsegood
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A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelective oxazolidine formation
This investigation has enjoyed the support of Loughborough University, the EPSRC, the University of East Anglia, and the ERDF (ISCE-Chem & INTERREG IVa programme 4061). We are indebted to the Royal Society for an Industry Fellowship (to PCBP) and the EPSRC national mass spectrometry service at the University of Wales, Swansea.