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|Title:||Efficient three-component synthesis of diversely substituted tetrahydro-1H-cyclopenta[c]quinolines|
|Keywords:||Povarov Reaction;cycloaddition;aldehydes;imines;alkenes;diastereoselectivity;scandium triflate;heterocycles;tetrahydroquinolines;multicomponent reaction;parallel synthesis|
|Abstract:||The synthesis of highly functionalized substituted tetrahydro-1H-cyclopenta[c]quinoline (I) and its reduced derivatives hexahydro-1H-cyclopenta[c]quinolines (II) via Povarov reaction in high diastereoselectivity and high to moderate yields is described herein. In addition, the relative stereochemistry of the α-substituent to the tetrahydroquinoline nitrogen, as well as the regioselectivity of reaction, is shown to depend upon subtle substituent effects on the aldehyde and aniline precursors. In most cases, a preference for the formation of endo diasteomeric adducts is observed but for reactions with ortho-substituted aldehydes, the formation of exo adducts is also observed. The exo-diastereoselectivity is found to be higher when the bulky size of this ortho group increases. Preparation of ortho and diortho-substituted aromatic aldehyde precursors of the Povarov reaction is also reported.|
|Appears in Collections:||IJC-B Vol.55B(07) [July 2016]|
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