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

Bulman Page, Philip C., Pearce, Christopher A., Chan, Yohan, Parker, Phillip, Buckley, Benjamin R., Rassias, Gerasimos A. and Elsegood, Mark R.J. (2015) Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols:Use as Catalysts in Enantioselective Asymmetric Epoxidation. Journal of Organic Chemistry, 80. pp. 8036-8045. ISSN 0022-3263

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 16 Oct 2015 14:07
Last Modified: 22 Apr 2020 00:32
URI: https://ueaeprints.uea.ac.uk/id/eprint/54717
DOI: 10.1021/acs.joc.5b01157

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