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

6 Citations (Scopus)

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

Fingerprint

Indoles
Cyclization
Sulfides
Stereoisomerism
Isomers
Cations
cyclodrine
indole

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Feldman, Ken S. ; Gonzalez, Inanllely Y. ; Glinkerman, Christopher M. / Indolidenes and Indolidenium Intermediates in the Synthesis of Cyclopent[b]indoles : Mechanistic Studies on Intramolecular Cyclizations. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 23. pp. 11849-11862.
@article{bdcc3d1c959d4df5a6e956f3c3857439,
title = "Indolidenes and Indolidenium Intermediates in the Synthesis of Cyclopent[b]indoles: Mechanistic Studies on Intramolecular Cyclizations",
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.",
author = "Feldman, {Ken S.} and Gonzalez, {Inanllely Y.} and Glinkerman, {Christopher M.}",
year = "2015",
month = "9",
day = "8",
doi = "10.1021/acs.joc.5b01777",
language = "English (US)",
volume = "80",
pages = "11849--11862",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "23",

}

Indolidenes and Indolidenium Intermediates in the Synthesis of Cyclopent[b]indoles : Mechanistic Studies on Intramolecular Cyclizations. / Feldman, Ken S.; Gonzalez, Inanllely Y.; Glinkerman, Christopher M.

In: Journal of Organic Chemistry, Vol. 80, No. 23, 08.09.2015, p. 11849-11862.

Research output: Contribution to journalArticle

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84948843931&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84948843931&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b01777

DO - 10.1021/acs.joc.5b01777

M3 - Article

AN - SCOPUS:84948843931

VL - 80

SP - 11849

EP - 11862

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -