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Unravelling the mechanism of the organocatalyzed aminolytic kinetic resolution of α-nitroepoxides: a theoretical study

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Abstract

The aminolytic kinetic resolution of 2-methyl-2-nitro-3-phenyl oxirane with aniline was investigated by quantum chemical computations. It has been assessed that the reaction proceeds via a concerted ring opening/elimination of nitrous acid mechanism. The results are in agreement with the experimental findings when using the Takemoto's catalyst, which is estimated to perform in a highly efficient manner in the kinetic resolution of this class of epoxides in the absence of any background reaction. H-Bonding, π–π and CH/π interactions appear to make a significant contribution to the formation of a ternary complex and a transition state, which preferentially facilitates the reaction of the (2R,3S)-nitroepoxide to the α-amino ketone, leaving (2S,3R)-nitroepoxide unreacted.

Graphical abstract: Unravelling the mechanism of the organocatalyzed aminolytic kinetic resolution of α-nitroepoxides: a theoretical study

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Article information


Submitted
05 Sep 2019
Accepted
13 Jan 2020
First published
16 Jan 2020

Catal. Sci. Technol., 2020, Advance Article
Article type
Paper

Unravelling the mechanism of the organocatalyzed aminolytic kinetic resolution of α-nitroepoxides: a theoretical study

A. Capobianco, S. Meninno and A. Lattanzi, Catal. Sci. Technol., 2020, Advance Article , DOI: 10.1039/C9CY01800J

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