Organocatalyzed Intramolecular Carbonyl-Ene Reactions

• Published in: Molecules (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
• Language: English
• 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

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...