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Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin
Journal article   Peer reviewed

Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

Philip C. Bulman Page, Yohan Chan, Abu Hassan Noor Armylisas and Mohammed Alahmdi
Tetrahedron, Vol.72(51), pp.8406-8416
22/12/2016
DOI: https://doi.org/10.1016/j.tet.2016.10.070

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin. (C) 2016 Elsevier Ltd. All rights reserved.

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