Abstract
We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
| Original language | English |
|---|---|
| Pages (from-to) | 8339-8343 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - 2019 Oct 18 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation. / Liou, Yan Cheng; Su, Yin Hsiang; Ku, Kuan Chun; Edukondalu, Athukuri; Lin, Chun Kai; Ke, You Syuan; Karanam, Praneeth; Lee, Chia Jui; Lin, Wenwei.
In: Organic Letters, Vol. 21, No. 20, 18.10.2019, p. 8339-8343.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation
AU - Liou, Yan Cheng
AU - Su, Yin Hsiang
AU - Ku, Kuan Chun
AU - Edukondalu, Athukuri
AU - Lin, Chun Kai
AU - Ke, You Syuan
AU - Karanam, Praneeth
AU - Lee, Chia Jui
AU - Lin, Wenwei
PY - 2019/10/18
Y1 - 2019/10/18
N2 - We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
AB - We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
UR - http://www.scopus.com/inward/record.url?scp=85073108596&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85073108596&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b03116
DO - 10.1021/acs.orglett.9b03116
M3 - Article
C2 - 31566385
AN - SCOPUS:85073108596
VL - 21
SP - 8339
EP - 8343
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 20
ER -