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

TETRAHEDRON

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Article

Page, Philip C. Bulman¹  Chan, Yohan¹  Armylisas, Abu Hassan Noor²  Alahmdi, Mohammed³ 

[1] Univ East Anglia, Sch Chem, Norwich Res Pk, Norwich NR4 7TJ, Norfolk, England

[2] Adv Oleochem Technol Div, Synth & Prod Dev Unit, 5,6 Persiaran Inst, Kajang 43000, Selangor, Malaysia

[3] Tabuk Univ, Dept Chem, POB 741, Tabuk 74191, Saudi Arabia

关键词: Asymmetric catalysis;    Iminium salt;    Enantioselective synthesis;    Chromene;    Mollugin;   

DOI  :  10.1016/j.tet.2016.10.070

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

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