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Issue 5, 2020
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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., 2020,10, 1422-1430
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, 10, 1422
DOI: 10.1039/C9CY01800J

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