TY - JOUR
T1 - Indolidenes and Indolidenium Intermediates in the Synthesis of Cyclopent[b]indoles
T2 - Mechanistic Studies on Intramolecular Cyclizations
AU - Feldman, Ken S.
AU - Gonzalez, Inanllely Y.
AU - Glinkerman, Christopher M.
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/9/8
Y1 - 2015/9/8
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.5b01777
DO - 10.1021/acs.joc.5b01777
M3 - Article
AN - SCOPUS:84948843931
SN - 0022-3263
VL - 80
SP - 11849
EP - 11862
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -