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
Schlagworte:	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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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo200556f