Organocatalyzed Intramolecular Carbonyl-Ene Reactions

An organocatalyzed intramolecular carbonyl-ene reaction was developed to produce carbocyclic and heterocyclic 5- and 6-membered rings from a citronellal-derived trifluoroketone and a variety of aldehydes. A phosphoramide derivative was found to promote the cyclization of the trifluoroketone, whereas...

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Published inMolecules (Basel, Switzerland) Vol. 21; no. 6; p. 713
Main Authors Dahlmann, Heidi A, McKinney, Amanda J, Santos, Maria P, Davis, Lindsey O
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 31.05.2016
MDPI
Subjects
Acids
Aldehydes - chemistry
carbonyl-ene
Catalysis
Communication
Cyclization
Ketones - chemistry
Molecular Structure
Monoterpenes - chemistry
N-triflylphosphoramide
Optimization
organocatalysis
Phosphoramides - chemistry
phosphoric acid
Stereoisomerism
organocatalysis
N-triflylphosphoramide
carbonyl-ene
phosphoric acid
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Summary:An organocatalyzed intramolecular carbonyl-ene reaction was developed to produce carbocyclic and heterocyclic 5- and 6-membered rings from a citronellal-derived trifluoroketone and a variety of aldehydes. A phosphoramide derivative was found to promote the cyclization of the trifluoroketone, whereas a less acidic phosphoric acid proved to be a superior catalyst for the aldehyde substrates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules21060713