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This article compares the diastereoselective epoxidation of acyclic and cyclic allylic alcohols, with the chemo- and diastereoselective olefinic oxidation of a range of acyclic and cyclic allylic amines. The diastereoselectivity in these systems is compared and a discussion about the origin of this high diastereocontrol is also presented. The ammonium directed epoxidation methodology has been extended to more complex substrates and representative applications of this protocol in natural product synthesis are also summarised.

Original publication

DOI

10.1039/c4ob00616j

Type

Journal article

Journal

Org Biomol Chem

Publication Date

14/07/2014

Volume

12

Pages

4544 - 4549