Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters:  Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes

• Published in: Journal of the American Chemical Society Vol. 127; no. 48; pp. 16804 - 16805
• Main Author: Zhang, Liming
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.12.2005; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; BENZANNULATION; 1,5-ENYNES; ISOMERIZATION; CATIONIC GOLD(I) COMPLEXES; CYCLOISOMERIZATION; 2-CYCLOPENTENONES; ALKYNES; REARRANGEMENTS; EFFICIENT; ENYNES; Intramolecular reaction; Chemical rearrangement; Catalytic reaction; Nitrogen heterocycle; Gold Complexes; Catalyst selectivity; Organic phosphine; Propargylic compound; Organic ligand; Transition metal Complexes; Complex catalyst; Experimental study; Tandem reaction; Dipolar cycloaddition; Bicyclic compound; Reaction mechanism; Chloro complex; Aromatic compound; Indole derivatives; Catalyst activity
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja056419c

The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and γ-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.