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- and Z-alkenyl sulfide isomers reveal a likely dichotomy of reaction paths that provide mixtures of both regioisomers and stereoisomers of the hexahydroindane adducts.
Department of Chemistry, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.
Ken S
KS
Feldman
Department of Chemistry, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.
Inanllely Y
IY
Gonzalez
Department of Chemistry, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.
Christopher M
CM
Glinkerman