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; Mohammed Alahmdi

doi:10.1016/j.tet.2016.10.070

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
, Mohammed Alahmdi

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

17 Downloads (Pure)

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.

Original language	English
Pages (from-to)	8406–8416
Number of pages	11
Journal	Tetrahedron
Volume	72
Issue number	51
Early online date	2 Nov 2016
DOIs	https://doi.org/10.1016/j.tet.2016.10.070
Publication status	Published - 22 Dec 2016

Keywords

Asymmetric catalysis
Iminium salt
Enantioselective synthesis
Chromene
Mollugin

Access to Document

10.1016/j.tet.2016.10.070

Accepted manuscriptAccepted author manuscript, 722 KBLicence: CC BY-NC-ND

Cite this

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

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.",

keywords = "Asymmetric catalysis, Iminium salt, Enantioselective synthesis, Chromene, Mollugin",

author = "\{Bulman Page\}, \{Philip C.\} and Yohan Chan and \{Noor Armylisas\}, \{Abu Hassan\} and Mohammed Alahmdi",

note = " Erratum available at http://dx.doi.org/10.1016/j.tet.2016.11.078",

year = "2016",

month = dec,

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doi = "10.1016/j.tet.2016.10.070",

language = "English",

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journal = "Tetrahedron",

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T1 - Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

AU - Bulman Page, Philip C.

AU - Chan, Yohan

AU - Noor Armylisas, Abu Hassan

AU - Alahmdi, Mohammed

N1 - Erratum available at http://dx.doi.org/10.1016/j.tet.2016.11.078

PY - 2016/12/22

Y1 - 2016/12/22

N2 - 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.

AB - 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.

KW - Asymmetric catalysis

KW - Iminium salt

KW - Enantioselective synthesis

KW - Chromene

KW - Mollugin

U2 - 10.1016/j.tet.2016.10.070

DO - 10.1016/j.tet.2016.10.070

M3 - Article

SN - 0040-4020

VL - 72

SP - 8406

EP - 8416

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -