Synlett 2016; 27(06): 854-858
DOI: 10.1055/s-0035-1560423
letter
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of Sulfonyl 2,5-Diaryltetrahydrofurans

M.-Y. Chang*
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, eMail: mychang@kmu.edu.tw
,
Y.-C. Cheng
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, eMail: mychang@kmu.edu.tw
› Institutsangaben
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Publikationsverlauf

Received: 24. November 2015

Accepted after revision: 23. Januar 2016

Publikationsdatum:
04. März 2016 (online)


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Abstract

BF3·OEt2-mediated stereocontrolled annulation of 4-alkenols affords sulfonyl 2,5-diaryltetrahydrofurans in good yields. The key synthetic route combines the facile stereoselective reduction of α-styryl-β-ketosulfones and an intramolecular Friedel–Crafts electrophilic cyclization of the resulting 4-alkenols. A plausible mechanism has been studied and proposed.

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