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2021•Russian Journal of Physical Chemistry ARequires access

Catalyst-Controlled Stereoselective Construction of Indole-Fused Heterocycles through Cycloadditions of Indolyl-Allenes: A Theoretical Investigation

Hongliang Ren

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Abstract

Abstract The mechanisms and stereoselectivity of Pt- and Au-catalyzed cycloaddition of N-(2-(1H-indol-1-yl)-ethyl)-N-(4-cyclopropyl-2-methylbuta-2,3-dien-1-yl)-4-methylbenzenesulfonamide have been theoretically investigated with the aid of density functional theory (DFT) calculations. Our results reveal that the rate- and stereoselectivity-determining step are both the tandem cyclization. The stereoselectivity observed in the experiment could be interpreted through our calculations. The steric and electronic properties of the cyclopropyl group account for the stereoselectivity.

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What this paper is about

Abstract The mechanisms and stereoselectivity of Pt- and Au-catalyzed cycloaddition of N-(2-(1H-indol-1-yl)-ethyl)-N-(4-cyclopropyl-2-methylbuta-2,3-dien-1-yl)-4-methylbenzenesulfonamide have been theoretically investigated with the aid of density functional theory (DFT) calculations. Our results reveal that the rate- and stereoselectivity-determining step are both the tandem cyclization. The stereoselectivity observed in the experiment could be interpreted through our calculations. The steric and electronic properties of the cyclopropyl group account for the stereoselectivity.

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Available abstract

Abstract The mechanisms and stereoselectivity of Pt- and Au-catalyzed cycloaddition of N-(2-(1H-indol-1-yl)-ethyl)-N-(4-cyclopropyl-2-methylbuta-2,3-dien-1-yl)-4-methylbenzenesulfonamide have been theoretically investigated with the aid of density functional theory (DFT) calculations. Our results reveal that the rate- and stereoselectivity-determining step are both the tandem cyclization. The stereoselectivity observed in the experiment could be interpreted through our calculations. The steric and electronic properties of the cyclopropyl group account for the stereoselectivity.

Key concepts: Stereoselectivity, Chemistry, Steric effects, Indole test, Cycloaddition, Density functional theory, Catalysis, Tandem

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Catalyst-Controlled Stereoselective Construction of Indole-Fused Heterocycles through Cycloadditions of Indolyl-Allenes: A Theoretical Investigation — Research Paper | ScholarLens