Abstract
It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.
Original language | English |
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Pages (from-to) | 5943-5946 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 51 |
Issue number | 45 |
DOIs | |
Publication status | Published - 2010 Nov 10 |
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Keywords
- Aldehyde
- Chemoselectivity
- Michael addition
- Morita-Baylis-Hillman
- Multicomponent reaction
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst. / Syu, Siang En; Wang, De Wei; Chen, Pei Yi; Hung, Yi Ting; Jhang, Yi Wun; Kao, Tzu Ting; Lee, Yu Ting; Lin, Wen-Wei.
In: Tetrahedron Letters, Vol. 51, No. 45, 10.11.2010, p. 5943-5946.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst
AU - Syu, Siang En
AU - Wang, De Wei
AU - Chen, Pei Yi
AU - Hung, Yi Ting
AU - Jhang, Yi Wun
AU - Kao, Tzu Ting
AU - Lee, Yu Ting
AU - Lin, Wen-Wei
PY - 2010/11/10
Y1 - 2010/11/10
N2 - It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.
AB - It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.
KW - Aldehyde
KW - Chemoselectivity
KW - Michael addition
KW - Morita-Baylis-Hillman
KW - Multicomponent reaction
UR - http://www.scopus.com/inward/record.url?scp=77957800141&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77957800141&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2010.09.020
DO - 10.1016/j.tetlet.2010.09.020
M3 - Article
AN - SCOPUS:77957800141
VL - 51
SP - 5943
EP - 5946
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 45
ER -