Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via the in situ formation of azomethine ylide followed by an intramolecular [3 + 2] cycloaddition reaction strategy. This protocol leads to the cre...

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Veröffentlicht in:Organic & biomolecular chemistry 2015-03, Vol.13 (10), p.2870-2874
Hauptverfasser: Bakthadoss, M, Kannan, D, Srinivasan, J, Vinayagam, V
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Sprache:eng
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Zusammenfassung:A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via the in situ formation of azomethine ylide followed by an intramolecular [3 + 2] cycloaddition reaction strategy. This protocol leads to the creation of two/three new rings and three/four contiguous stereocentres, in which one of them is a tetra-substituted carbon center, in a highly diastereoselective fashion with excellent yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob02203c