Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions

Keita Takubo; Ahmed Mohamed; Takafumi Ide; Kazuyuki Saito; Takashi Ikawa; Takehiko Yoshimitsu; Shuji Akai

doi:10.1021/acs.joc.7b02208

Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions

Keita Takubo, Ahmed Mohamed, Takafumi Ide, Kazuyuki Saito, Takashi Ikawa, Takehiko Yoshimitsu, Shuji Akai

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

Abstract

The dienone-phenol rearrangement is a useful tool for the synthesis of highly substituted phenols. In our previous study of the rearrangement of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienone under deoxyfluorination conditions, bond migration proceeded with very poor regioselectivity. In this paper, an acid-mediated rearrangement of O-perfluoroalkylsulfonyl difluorides with regioselective migration toward the β′-carbon is reported. This method allowed the synthesis of a fluorinated analog of allocolchicinoids with improved total yield. Successful application to other substrates was also demonstrated.

Original language	English
Pages (from-to)	13141-13151
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	82
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.7b02208
Publication status	Published - Dec 15 2017
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions. / Takubo, Keita; Mohamed, Ahmed; Ide, Takafumi; Saito, Kazuyuki; Ikawa, Takashi; Yoshimitsu, Takehiko; Akai, Shuji.

In: Journal of Organic Chemistry, Vol. 82, No. 24, 15.12.2017, p. 13141-13151.

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

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