Indolidenes and Indolidenium Intermediates in the Synthesis of Cyclopent[b]indoles: Mechanistic Studies on Intramolecular Cyclizations

Tetracyclic products featuring predominantly a trans-hexahydroindane unit annelated onto the C(2)/C(3) positions of indole can be accessed by intramolecular cyclocondensation of tethered alkenyl sulfides with either indolidene or indolidenium cation intermediates. Studies with geometrically pure E-...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-12, Vol.80 (23), p.11849-11862
Main Authors: Feldman, Ken S., Gonzalez, Inanllely Y., Glinkerman, Christopher M.
Format: Article
Language:English
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Summary:Tetracyclic products featuring predominantly a trans-hexahydroindane unit annelated onto the C(2)/C(3) positions of indole can be accessed by intramolecular cyclocondensation of tethered alkenyl sulfides with either indolidene or indolidenium cation intermediates. Studies with geometrically pure E- and Z-alkenyl sulfide isomers reveal a likely dichotomy of reaction paths that provide mixtures of both regioisomers and stereoisomers of the hexahydroindane adducts.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01777