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- Title
Phase transfer catalyzed conjugate addition-initiated ring-closure (CAIRC) reactions with 2-bromo-2-cyclopentenones.
- Authors
Yirsaw, Alemayehu Mekonnen; Carlson, Rolf Eric
- Abstract
When 2-bromo-2-cyclopentenone is treated with various carbon nucleophiles containing active methylenes, it undergoes a conjugate addition initiated-ring closure (CAIRC) reaction. This leads to the formation of carboand heterocyclic compounds in a regioselective fashion with good to high yield. Several bases and phase transfer catalysts were investigated. CsF-Si(OEt)4 as base together with benzyldimethyl (2-hydroxyethyl)- ammonium chloride, C6H5CH2N(Cl)(CH3)2CH2CH2OH, as phase transfer catalyst, were found to be mild and efficient reagents for carrying out the synthetic transformation.
- Subjects
PHASE-transfer catalysis; CYCLOPENTENONE; DIHYDROFURANS; CYCLOPROPANE; ADDITION reactions
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2017, Vol 2017, p74
- ISSN
1551-7004
- Publication type
Article
- DOI
10.3998/ark.5550190.p009.911