Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in Enantioselective Asymmetric Epoxidation

Philip C Bulman Page; Christopher A Pearce; Yohan Chan; Phillip Parker; Benjamin R Buckley; Gerasimos A Rassias; Mark R J Elsegood

doi:10.1021/acs.joc.5b01157

Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in Enantioselective Asymmetric Epoxidation

J Org Chem. 2015 Aug 21;80(16):8036-45. doi: 10.1021/acs.joc.5b01157. Epub 2015 Aug 3.

Authors

Philip C Bulman Page¹, Christopher A Pearce¹, Yohan Chan¹, Phillip Parker², Benjamin R Buckley², Gerasimos A Rassias³, Mark R J Elsegood²

Affiliations

¹ †School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, Norfolk NR4 7TJ, U.K.
² ‡Chemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, U.K.
³ §Department of Chemistry, University of Patras, 26504 Patras, Greece.

PMID: 26204427
DOI: 10.1021/acs.joc.5b01157

Abstract

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.