Selective Gold(I)-Catalyzed Formation of Tetracyclic Indolines: A Single Transition Structure and Bifurcations Lead to Multiple Products

Selective Gold(I)-Catalyzed Formation of Tetracyclic Indolines: A Single Transition Structure and Bifurcations Lead to Multiple Products

Several alkynylindoles undergo gold(I)-catalyzed cyclization reactions to form a single isomer in each case. Density functional theory shows why this reaction is favored over the many possible regio- and stereoisomeric reaction pathways. This transformation involves a two-step no-intermediate mechan...

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Veröffentlicht in:Journal of organic chemistry 2011-05, Vol.76 (9), p.3477-3483
Hauptverfasser: Noey, Elizabeth L, Wang, Xiang, Houk, K. N
Format: Artikel
Sprache:eng
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Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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container_title Journal of organic chemistry
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creator Noey, Elizabeth L
Wang, Xiang
Houk, K. N
description Several alkynylindoles undergo gold(I)-catalyzed cyclization reactions to form a single isomer in each case. Density functional theory shows why this reaction is favored over the many possible regio- and stereoisomeric reaction pathways. This transformation involves a two-step no-intermediate mechanism with surface bifurcations leading to two or three products. Such bifurcations could explain reactivity in many gold(I)-catalyzed enyne cyclization reactions.
doi_str_mv 10.1021/jo200556f
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source American Chemical Society Journals
subjects Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
title Selective Gold(I)-Catalyzed Formation of Tetracyclic Indolines: A Single Transition Structure and Bifurcations Lead to Multiple Products
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