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Substrate-controlled, PBu3-catalyzed annulation of phenacylmalononitriles with allenoates enables tunable access to cyclopentenes
- Source :
- Chemical Communications. 56:11054-11057
- Publication Year :
- 2020
- Publisher :
- Royal Society of Chemistry (RSC), 2020.
-
Abstract
- Divergence in the PBu3-catalyzed [3+2] annulation of phenacylmalononitriles with allenoates, controlled by the γ-substitution on allenoates, offers a tunable synthesis of multifunctionalized cyclopentene carboxamides and cyclopentenols. An unprecedented formation of cyclopentene carboxamide was observed when allenic esters bearing a substitution at the γ-position were employed, while unsubstituted allenoates produced cyclopentenols. The former reaction likely involves a Michael/aldol/nucleophilic cyclization sequence in a domino manner.
- Subjects :
- Annulation
medicine.drug_class
Metals and Alloys
Substrate (chemistry)
Carboxamide
General Chemistry
Combinatorial chemistry
Catalysis
Domino
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
chemistry.chemical_compound
Aldol reaction
chemistry
Nucleophile
Materials Chemistry
Ceramics and Composites
medicine
Cyclopentene
Subjects
Details
- ISSN :
- 1364548X and 13597345
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Chemical Communications
- Accession number :
- edsair.doi...........a962ee6f48e47a3154e912f48e522cf4