Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines provides a novel method for preparation of 2-trifluoromethyl-tetrahydro-pyran derivatives in good yields. l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines prov...

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Published inJournal of fluorine chemistry Vol. 130; no. 5; pp. 488 - 492
Main Authors Zhang, Jun, Zhang, Min, Cao, Weiguo, Song, Liping, Qian, Qun, Tan, Jiwen, Shao, Min
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 01.05.2009
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Fluorinated heterocycles
Functionalized tetrahydropyran
One-pot three-component reaction
Physical Sciences
Science & Technology
One-pot three-component reaction
Fluorinated heterocycles
Functionalized tetrahydropyran
ALCOHOLS
ASYMMETRIC ALPHA-AMINATION
ALDER REACTIONS
PRINS-TYPE CYCLIZATION
DOMINO SYNTHESIS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
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Summary:l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines provides a novel method for preparation of 2-trifluoromethyl-tetrahydro-pyran derivatives in good yields. l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines provide a novel method for preparation of ethyl-6-(arylamino)-2-hydroxy-4-phenyl-2-(trifluoromethyl)tetrahydro-2H-pyran-3-carboxylate derivatives in good yields. The reaction was conducted by initial Michael addition, followed by intra-molecular cyclization under mild conditions. The structure of a typical ethyl-2-hydroxy-4-phenyl-6-( m-tolylamino)-2-(trifluoromethyl)tetrahydro-2H-pyran-3-carboxylate ( 4h) was confirmed by XRD analysis. A plausible mechanism is presented.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2009.02.016