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 in | Molecules (Basel, Switzerland) Vol. 21; no. 6; p. 713 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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31.05.2016
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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. |
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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.) |
Author_xml | – sequence: 1 givenname: Heidi A surname: Dahlmann fullname: Dahlmann, Heidi A email: hdahlmann@berry.edu organization: Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. hdahlmann@berry.edu – sequence: 2 givenname: Amanda J surname: McKinney fullname: McKinney, Amanda J email: amanda.mckinney@vikings.berry.edu organization: Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. amanda.mckinney@vikings.berry.edu – sequence: 3 givenname: Maria P surname: Santos fullname: Santos, Maria P email: maria.santos@vikings.berry.edu organization: Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. maria.santos@vikings.berry.edu – sequence: 4 givenname: Lindsey O surname: Davis fullname: Davis, Lindsey O email: ldavis@berry.edu organization: Department of Chemistry and Biochemistry, Berry College, P.O. Box 495016, Mt. Berry, GA 30149, USA. ldavis@berry.edu |
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 10.1021/jo9821675 10.5012/bkcs.2010.31.03.539 10.2174/1385272003376274 10.1021/jo00044a029 10.1016/S0040-4039(98)00115-4 10.1002/hlca.19780610416 10.1002/chem.200390042 10.1021/ol202009x 10.1021/jo00118a035 10.1021/jo052532+ 10.1016/j.tet.2008.06.075 10.1021/jo060495w 10.1002/anie.200802139 10.1021/jo00444a011 10.1021/cr068373r 10.1002/chem.201101157 10.1002/anie.200500154 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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