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Title: Efficient three-component synthesis of diversely substituted tetrahydro-1H-cyclopenta[c]quinolines
Authors: Niño, Patricia
Cabaa, Marta
Aguilar, Nuria
Terricabras, Emma
Albericio, Fernando
Fernàndez, Joan-Carles
Keywords: Povarov Reaction;cycloaddition;aldehydes;imines;alkenes;diastereoselectivity;scandium triflate;heterocycles;tetrahydroquinolines;multicomponent reaction;parallel synthesis
Issue Date: Jul-2016
Publisher: NISCAIR-CSIR, India
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.
Page(s): 854-881
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.55B(07) [July 2016]

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