Silver Dependent Enantiodivergent Gold(I) Catalysed Asymmetric Intramolecular Hydroamination of Alkenes: A Theoretical Study - Archive ouverte HAL Access content directly
Journal Articles Catalysts Year : 2022

Silver Dependent Enantiodivergent Gold(I) Catalysed Asymmetric Intramolecular Hydroamination of Alkenes: A Theoretical Study

Abstract

We report a theoretical study of the first silver-dependent enantiodivergent gold-catalysed reaction. The combination of a single chiral binuclear gold(I) chloride complex and silver perchlorate catalyses the asymmetric intramolecular hydroamination of alkenes and affords both enantiomers of the products by applying a simple solvent change from toluene to methanol. A goldsilver chloride adduct that occurs only in methanol appears to control the enantioinversion. If one gold atom coordinates and activates the alkene moiety, the other gold is included in an adduct with silver chloride, which coordinates a methanol solvent molecule and further interacts with the amine function. If the use of toluene implies free anions and affords (S)-enantiomer, methanol allows a proximal interaction with the amine, leads to an opposite stereodifferentiation of the two diastereomeric intermediates during the final protodeauration step and results in the (R)-enantiomer.
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hal-03852460 , version 1 (15-11-2022)

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Ruchi Dixit, Himanshu Sharma, Francine Agbossou-Niedercorn, Kumar Vanka, Christophe Michon. Silver Dependent Enantiodivergent Gold(I) Catalysed Asymmetric Intramolecular Hydroamination of Alkenes: A Theoretical Study. Catalysts, 2022, This article belongs to the Special Issue Recent Applications of Metal Catalysts in Organic Syntheses, 12 (11), pp.1392. ⟨10.3390/catal12111392⟩. ⟨hal-03852460⟩
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