Synthesis 2018; 50(24): 4796-4808
DOI: 10.1055/s-0037-161114
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of 4-Amino-3-hydroxybenzopyran Flavanol Derivatives from Chalcones

Qiwen Gao
Lianyan L. Xu
Vincent P. Parise
Yash R. Mehta
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St., Chicago, IL 60607, USA   Email: [email protected]
› Author Affiliations
Funding was provided by the UIC Department of Chemistry.
Further Information

Publication History

Received: 05 October 2018

Accepted after revision: 12 October 2018

Publication Date:
21 November 2018 (online)


A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.

Supporting Information

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