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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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.
AbstractList 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.
Author Davis, Lindsey O
McKinney, Amanda J
Santos, Maria P
Dahlmann, Heidi A
AuthorAffiliation Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA; hdahlmann@berry.edu (H.A.D.); amanda.mckinney@vikings.berry.edu (A.J.M.); maria.santos@vikings.berry.edu (M.P.S.)
AuthorAffiliation_xml – name: Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA; hdahlmann@berry.edu (H.A.D.); amanda.mckinney@vikings.berry.edu (A.J.M.); maria.santos@vikings.berry.edu (M.P.S.)
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  givenname: Amanda J
  surname: McKinney
  fullname: McKinney, Amanda J
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  fullname: Santos, Maria P
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/27258238$$D View this record in MEDLINE/PubMed
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Cites_doi 10.1055/s-1978-24696
10.1021/jacs.5b09484
10.1021/jo801737c
10.1002/anie.200704439
10.1021/jo00144a027
10.1002/anie.200301732
10.1246/cl.2008.654
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10.5012/bkcs.2010.31.03.539
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10.1021/jo00044a029
10.1016/S0040-4039(98)00115-4
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10.1002/chem.201001438
10.1021/ar50155a007
10.1186/1860-5397-3-24
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Keywords organocatalysis
N-triflylphosphoramide
carbonyl-ene
phosphoric acid
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SubjectTerms Acids
Aldehydes - chemistry
carbonyl-ene
Catalysis
Communication
Cyclization
Ketones - chemistry
Molecular Structure
Monoterpenes - chemistry
N-triflylphosphoramide
Optimization
organocatalysis
Phosphoramides - chemistry
phosphoric acid
Stereoisomerism
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Title Organocatalyzed Intramolecular Carbonyl-Ene Reactions
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