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Organocatalyzed Intramolecular Carbonyl-Ene Reactions.

ABSTRACT: 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.

SUBMITTER: Dahlmann HA

PROVIDER: S-EPMC6272844 | biostudies-other | 2016 May

REPOSITORIES: biostudies-other

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Organocatalyzed Intramolecular Carbonyl-Ene Reactions.

Dahlmann Heidi A HA McKinney Amanda J AJ Santos Maria P MP Davis Lindsey O LO

Molecules (Basel, Switzerland) 20160531 6

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. ...[more]

PMID: 27258238

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