Intramolecular [3 + 2] cyclocondensations of alkenes with indolidenes and indolidenium cations

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

doi:10.1021/ja508421e

Intramolecular [3 + 2] cyclocondensations of alkenes with indolidenes and indolidenium cations

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

Chemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

C(2)-C(3) cyclopentannelated indole constructs are prepared by either (a) a cyclization cascade of an alkenyl sulfide tethered to a 2-azido-1-allenylbenzene core or (b) cationic cyclization of a tethered alkenyl sulfide with a putative 2-indolidenium cation. In both cases, issues of C-C versus C-N bond formation emerge, and the results indicate that the former is favored.

Original language	English (US)
Pages (from-to)	15138-15141
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	43
DOIs	https://doi.org/10.1021/ja508421e
State	Published - Oct 29 2014

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja508421e

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title = "Intramolecular [3 + 2] cyclocondensations of alkenes with indolidenes and indolidenium cations",

abstract = "C(2)-C(3) cyclopentannelated indole constructs are prepared by either (a) a cyclization cascade of an alkenyl sulfide tethered to a 2-azido-1-allenylbenzene core or (b) cationic cyclization of a tethered alkenyl sulfide with a putative 2-indolidenium cation. In both cases, issues of C-C versus C-N bond formation emerge, and the results indicate that the former is favored.",

author = "Feldman, {Ken S.} and Gonzalez, {Inanllely Y.} and Glinkerman, {Christopher M.}",

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T1 - Intramolecular [3 + 2] cyclocondensations of alkenes with indolidenes and indolidenium cations

AU - Feldman, Ken S.

AU - Gonzalez, Inanllely Y.

AU - Glinkerman, Christopher M.

PY - 2014/10/29

Y1 - 2014/10/29

N2 - C(2)-C(3) cyclopentannelated indole constructs are prepared by either (a) a cyclization cascade of an alkenyl sulfide tethered to a 2-azido-1-allenylbenzene core or (b) cationic cyclization of a tethered alkenyl sulfide with a putative 2-indolidenium cation. In both cases, issues of C-C versus C-N bond formation emerge, and the results indicate that the former is favored.

AB - C(2)-C(3) cyclopentannelated indole constructs are prepared by either (a) a cyclization cascade of an alkenyl sulfide tethered to a 2-azido-1-allenylbenzene core or (b) cationic cyclization of a tethered alkenyl sulfide with a putative 2-indolidenium cation. In both cases, issues of C-C versus C-N bond formation emerge, and the results indicate that the former is favored.

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JF - Journal of the American Chemical Society

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Intramolecular [3 + 2] cyclocondensations of alkenes with indolidenes and indolidenium cations

Abstract

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