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

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 aminoalco...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2015-08, Vol.80 (16), p.8036-8045
Main Authors: Bulman Page, Philip C, Pearce, Christopher A, Chan, Yohan, Parker, Phillip, Buckley, Benjamin R, Rassias, Gerasimos A, Elsegood, Mark R. J
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01157