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 a less acidic phosphoric acid proved to be a superior catalyst for the aldehyde substrates.
Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. hdahlmann@berry.edu.
Heidi A
HA
Dahlmann
Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. amanda.mckinney@vikings.berry.edu.
Amanda J
AJ
McKinney
Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. maria.santos@vikings.berry.edu.
Maria P
MP
Santos
Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. ldavis@berry.edu.
Lindsey O
LO
Davis
D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D063088:Phosphoramides / Q000737:chemistry*; D013237:Stereoisomerism
D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D007659:Ketones; D039821:Monoterpenes; D063088:Phosphoramides; C005438:phosphoramide; C108217:citronellal
N-triflylphosphoramide; carbonyl-ene; organocatalysis; phosphoric acid