Gold(I)‐katalysierte Cycloisomerisierung von 3‐Alkoxy‐1,6‐diinen: ein einfacher Zugang zu Bicyclo[2.2.1]hept‐5‐en‐2‐onen

Hu, Chao; Wang, Tao; Rudolph, Matthias; Oeser, Thomas; Asiri, Abdullah M.; Hashmi, A. Stephen K.

doi:10.1002/ange.201914284

Angewandte Chemie

2020

DOI: 10.1002/ange.201914284

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Gold(I)‐katalysierte Cycloisomerisierung von 3‐Alkoxy‐1,6‐diinen: ein einfacher Zugang zu Bicyclo[2.2.1]hept‐5‐en‐2‐onen

Chao Hu

Tao Wang

Matthias Rudolph

et al.

Abstract: Eine neue Gold‐katalysierte Cycloisomerisierung von 1,6‐diinen wurde entwickelt, die einen atomökonomischen Zugang zu einem Satz verschiedenster Bicyclo[2.2.1]hept‐5‐en‐2‐onen in moderaten bis guten Ausbeuten darstellt. Für unsymmetrische Edukte mit zwei verschiedenen internen Alkinyl‐Substituenten konnte in einem gewissen Ausmaß die Regioselektivität sowohl durch elektronische als auch durch sterische Faktoren kontrolliert werden. Dieses neue Reaktivitätsmuster kann als Grundlage für neue und unkonventionelle… Show more

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Cited by 3 publications

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Gold(I)‐Catalyzed Regioselective Cycloisomerization of Bis(Indol‐3‐Yl)‐Ynamides to Access Five‐Membered Ring Linked Bisindole Derivatives

Xiao,

Wei,

Shi

2024

Adv Synth Catal

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A gold(I)‐catalyzed regioselective cycloisomerization of bis(indol‐3‐yl)‐ynamides for the rapid construction of five‐membered ring linked bisindole derivatives has been reported, affording the desired products in the range of 72% ‐ 94% yields under mild conditions along with broad substrate scope. Moreover, DFT calculation of the NBO (natural bond orbital) charge supports the origin of its regioselectivity.

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Gold(I)‐Catalyzed Regioselective Cycloisomerization of Bis(Indol‐3‐Yl)‐Ynamides to Access Five‐Membered Ring Linked Bisindole Derivatives

Xiao,

Wei,

Shi

2024

Adv Synth Catal

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show abstract

I₂‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

Zhu

Nie

et al. 2023

Angewandte Chemie

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Herein, an I 2 -catalyzed unprecedented cycloisomerization of ynamides is developed, furnishing various functionalized bis(indole) derivatives in generally good to excellent yields with wide substrate scope and excellent atom-economy. This protocol not only represents the first molecular-iodine-catalyzed tandem complex alkyne cycloisomerizations, but also constitutes the first chemoselective cycloisomerization of tryptamine-ynamides involving distinctively different C-(sp 3 )À C(sp 3 ) bond cleavage and rearrangement. Moreover, chiral tetrahydropyridine frameworks containing two stereocenters are obtained with moderate to excellent diastereoselectivities and excellent enantioselectivities. Meanwhile, cycloisomerization and aromatization of ynamides produce pyrrolyl indoles with high efficiency enabled by I 2 . Additionally, control experiments and theoretical calculations reveal that this reaction probably undergoes a tandem 5-exo-dig cyclization/rearrangement process.

show abstract

I₂‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

Zhu

Nie

et al. 2023

Angew Chem Int Ed

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show abstract

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Gold(I)‐katalysierte Cycloisomerisierung von 3‐Alkoxy‐1,6‐diinen: ein einfacher Zugang zu Bicyclo[2.2.1]hept‐5‐en‐2‐onen

Cited by 3 publications

References 85 publications

Gold(I)‐Catalyzed Regioselective Cycloisomerization of Bis(Indol‐3‐Yl)‐Ynamides to Access Five‐Membered Ring Linked Bisindole Derivatives

Gold(I)‐Catalyzed Regioselective Cycloisomerization of Bis(Indol‐3‐Yl)‐Ynamides to Access Five‐Membered Ring Linked Bisindole Derivatives

I₂‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

I₂‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

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Gold(I)‐katalysierte Cycloisomerisierung von 3‐Alkoxy‐1,6‐diinen: ein einfacher Zugang zu Bicyclo[2.2.1]hept‐5‐en‐2‐onen

Cited by 3 publications

References 85 publications

Gold(I)‐Catalyzed Regioselective Cycloisomerization of Bis(Indol‐3‐Yl)‐Ynamides to Access Five‐Membered Ring Linked Bisindole Derivatives

Gold(I)‐Catalyzed Regioselective Cycloisomerization of Bis(Indol‐3‐Yl)‐Ynamides to Access Five‐Membered Ring Linked Bisindole Derivatives

I2‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

I2‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

Contact Info

Product

Resources

About

I₂‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives

I₂‐Catalyzed Cycloisomerization of Ynamides: Chemoselective and Divergent Access to Indole Derivatives