Iminium ion cascade reactions: stereoselective synthesis of quinolizidines and indolizidines
نویسندگان
چکیده
منابع مشابه
Indolizidines and quinolizidines: natural products and beyond
Alkaloids occur in such astonishing profusion in nature that one tends to forget that they are assembled from a relatively small number of structural motifs. Among the motifs that are most frequently encountered are bicyclic systems containing bridgehead nitrogen, especially 1azabicyclo[4.3.0]nonanes and 1-azabicyclo[4.4.0]decanes or their unsaturated analogues – the indolizidines and quinolizi...
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The assembly of complex spirocyclopentaneoxindoles via a novel organocatalytic iminium-enamine cascade process is reported. Reactions between 3-substituted oxindoles and α,β-unsaturated aldehydes catalyzed by second generation prolinol ethers provided the desired products in high yield with excellent levels of enantioselectivity in a single step.
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Iminoacetonitriles participate as reactive dienophiles in intermolecular and intramolecular DielsAlder cycloadditions leading to quinolizidines, indolizidines, and piperidines. The resultant aamino nitrile cycloadducts are versatile synthetic intermediates which can be further elaborated by stereoselective alkylation, reduction, reductive cyclization, and Bruylants reactions. The first part of ...
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A reliable synthetic route to fused polycyclic indolines is documented by the development of a stereoselective gold catalyzed cascade cyclization of indole propargylic alcohols.
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A [3 + 3] annelation of enantiomerically pure aziridine 7 provides the functionalised piperidine 8 that can be elaborated to the indolizidine skeleton in only 4 steps with good stereocontrol.
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ژورنال
عنوان ژورنال: Tetrahedron
سال: 2009
ISSN: 0040-4020
DOI: 10.1016/j.tet.2008.10.074