Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 23, Pages 11849-11862Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01777
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Funding
- Chemical Synthesis Division of the National Science Foundation [CHE1361260]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361260] Funding Source: National Science Foundation
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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.
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