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 | |
| Publication status | Published - Dec 15 2017 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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
}
TY - JOUR
T1 - Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions
AU - Takubo, Keita
AU - Mohamed, Ahmed
AU - Ide, Takafumi
AU - Saito, Kazuyuki
AU - Ikawa, Takashi
AU - Yoshimitsu, Takehiko
AU - Akai, Shuji
PY - 2017/12/15
Y1 - 2017/12/15
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85038415134&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85038415134&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02208
DO - 10.1021/acs.joc.7b02208
M3 - Article
AN - SCOPUS:85038415134
VL - 82
SP - 13141
EP - 13151
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 24
ER -