Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX).

Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX). Research Abstract Details 

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Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX). Abstract Text:

Youqing Yu,Wei Shen,Jinsheng Zhang,Rongxing He,Ming Li,

The mechanism of the direct amination of beta-keto esters catalyzed by copper(II)-bisoxazoline has been studied by means of density functional theory of B3LYP method. The computational results support the present mechanism, which involves (i) the generation of the enol from beta-keto esters, which coordinates to copper(II)-bisoxazoline. The coordination step appears to be fast, exothermic, and irreversible. (ii) The formation of the sigma(N-C) bond via a six-membered ring transition state after azo dicarboxylate coordination with the chiral catalyst. This step is chirality-control step. (iii) Intramolecular hydrogen migration generates a catalyst-product complex, which can finally yield product. The hydrogen shift is the rate-determining step, which affords the experimentally observed (R)-product. The stereochemical predictions have been rationalized in terms of steric repulsions, showing good agreement with experimental data.

Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX). Publishing Authors By Initials

Y Yu,W Shen,J Zhang,R He,M Li,

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Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX). Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of molecular modeling

VOLUME: 14

Page Numbers: 237-47

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ISSN: 0948-5023

DAY: 29

MONTH: 01

YEAR: 2008

Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX). Information

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LANGUAGE: eng

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Grant and Affiliation Information for Theoretical investigation of direct amination of beta-ketoesters catalyzed by copper(II)-bisoxazoline(BOX).

AFFILIATION: Department of Chemistry, Southwest University, Chongqing, 400715, People's Republic of China.

Country: Germany

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MEDLINETA: J Mol Model

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