Abstract
An efficient organocatalytic method was developed for synthesizing functionalized spiropyrazolone derivatives containing four contiguous stereogenic centres by using a Michael-aldol consecutive reaction. We applied a quinine-derived squaramide catalyst to catalyze a reaction between 3-methyl-1-aryl-2-pyrazolin-5-ones and (E)-5-nitro-6-aryl-hex-5-en-2-ones, realizing the desired spiropyrazolones in moderate-to-good yields (up to 80%) with good-to-excellent stereoselectivities (up to >20:1 dr, 94% ee).
| Original language | English |
|---|---|
| Pages (from-to) | 77474-77480 |
| Number of pages | 7 |
| Journal | RSC Advances |
| Volume | 6 |
| Issue number | 81 |
| DOIs | |
| Publication status | Published - 2016 Jan 1 |
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ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)
Cite this
Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones : Via a Michael-aldol sequential reaction. / Amireddy, Mamatha; Chen, Kwunmin.
In: RSC Advances, Vol. 6, No. 81, 01.01.2016, p. 77474-77480.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones
T2 - Via a Michael-aldol sequential reaction
AU - Amireddy, Mamatha
AU - Chen, Kwunmin
PY - 2016/1/1
Y1 - 2016/1/1
N2 - An efficient organocatalytic method was developed for synthesizing functionalized spiropyrazolone derivatives containing four contiguous stereogenic centres by using a Michael-aldol consecutive reaction. We applied a quinine-derived squaramide catalyst to catalyze a reaction between 3-methyl-1-aryl-2-pyrazolin-5-ones and (E)-5-nitro-6-aryl-hex-5-en-2-ones, realizing the desired spiropyrazolones in moderate-to-good yields (up to 80%) with good-to-excellent stereoselectivities (up to >20:1 dr, 94% ee).
AB - An efficient organocatalytic method was developed for synthesizing functionalized spiropyrazolone derivatives containing four contiguous stereogenic centres by using a Michael-aldol consecutive reaction. We applied a quinine-derived squaramide catalyst to catalyze a reaction between 3-methyl-1-aryl-2-pyrazolin-5-ones and (E)-5-nitro-6-aryl-hex-5-en-2-ones, realizing the desired spiropyrazolones in moderate-to-good yields (up to 80%) with good-to-excellent stereoselectivities (up to >20:1 dr, 94% ee).
UR - http://www.scopus.com/inward/record.url?scp=85025619718&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85025619718&partnerID=8YFLogxK
U2 - 10.1039/c6ra13923j
DO - 10.1039/c6ra13923j
M3 - Article
VL - 6
SP - 77474
EP - 77480
JO - RSC Advances
JF - RSC Advances
SN - 2046-2069
IS - 81
ER -