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

Ken S. Feldman, Inanllely Y. Gonzalez, Christopher M. Glinkerman

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)11849-11862
Number of pages14
JournalJournal of Organic Chemistry
Volume80
Issue number23
DOIs
StatePublished - Sep 8 2015

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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