Abstract
An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.
| Original language | English |
|---|---|
| Pages (from-to) | 5156-5161 |
| Number of pages | 6 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 11 |
| Issue number | 31 |
| DOIs | |
| Publication status | Published - 2013 Aug 21 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions : Mechanism and theoretical analysis. / Lee, Yu Ting; Lee, Yen Te; Lee, Chia Jui; Sheu, Chia Ning; Lin, Bo Yu; Wang, Jeng Han; Lin, Wenwei.
In: Organic and Biomolecular Chemistry, Vol. 11, No. 31, 21.08.2013, p. 5156-5161.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions
T2 - Mechanism and theoretical analysis
AU - Lee, Yu Ting
AU - Lee, Yen Te
AU - Lee, Chia Jui
AU - Sheu, Chia Ning
AU - Lin, Bo Yu
AU - Wang, Jeng Han
AU - Lin, Wenwei
PY - 2013/8/21
Y1 - 2013/8/21
N2 - An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.
AB - An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.
UR - http://www.scopus.com/inward/record.url?scp=84880645907&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84880645907&partnerID=8YFLogxK
U2 - 10.1039/c3ob40858b
DO - 10.1039/c3ob40858b
M3 - Article
C2 - 23817532
AN - SCOPUS:84880645907
VL - 11
SP - 5156
EP - 5161
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 31
ER -