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

Bulman Page, Philip C., Chan, Yohan, Noor Armylisas, Abu Hassan and Alahmdi, Mohammed (2016) Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin. Tetrahedron, 72 (51). 8406–8416. ISSN 0040-4020

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Abstract

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.

Item Type:	Article
Additional Information:	Erratum available at http://dx.doi.org/10.1016/j.tet.2016.11.078
Uncontrolled Keywords:	asymmetric catalysis,iminium salt,enantioselective synthesis,chromene,mollugin
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Pure Connector
Date Deposited:	03 Nov 2016 17:00
Last Modified:	25 Sep 2024 12:21
URI:	https://ueaeprints.uea.ac.uk/id/eprint/61241
DOI:	10.1016/j.tet.2016.10.070

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