Abstract
A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.
| Original language | English |
|---|---|
| Pages (from-to) | 12702-12705 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 54 |
| Issue number | 90 |
| DOIs | |
| Publication status | Published - 2018 Jan 1 |
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ASJC Scopus subject areas
- Catalysis
- Electronic, Optical and Magnetic Materials
- Ceramics and Composites
- Chemistry(all)
- Surfaces, Coatings and Films
- Metals and Alloys
- Materials Chemistry
Cite this
3-Homoacyl coumarin : An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition. / Chen, Yi Ru; Ganapuram, Madhusudhan Reddy; Hsieh, Kai Hong; Chen, Kai Han; Karanam, Praneeth; Vagh, Sandip Sambhaji; Liou, Yan Cheng; Lin, Wen-Wei.
In: Chemical Communications, Vol. 54, No. 90, 01.01.2018, p. 12702-12705.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 3-Homoacyl coumarin
T2 - An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition
AU - Chen, Yi Ru
AU - Ganapuram, Madhusudhan Reddy
AU - Hsieh, Kai Hong
AU - Chen, Kai Han
AU - Karanam, Praneeth
AU - Vagh, Sandip Sambhaji
AU - Liou, Yan Cheng
AU - Lin, Wen-Wei
PY - 2018/1/1
Y1 - 2018/1/1
N2 - A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.
AB - A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.
UR - http://www.scopus.com/inward/record.url?scp=85056306826&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85056306826&partnerID=8YFLogxK
U2 - 10.1039/c8cc07271j
DO - 10.1039/c8cc07271j
M3 - Article
C2 - 30370907
AN - SCOPUS:85056306826
VL - 54
SP - 12702
EP - 12705
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 90
ER -