Base-catalyzed inversion of chiral sulfur centers. A computational study

David Balcells; Feliu Maseras; Noureddine Khiar

doi:10.1021/ol0493507

Base-catalyzed inversion of chiral sulfur centers. A computational study

David Balcells, Feliu Maseras, Noureddine Khiar

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

17 Citations (Scopus)

Abstract

A theoretical study on the pyramidal inversion of the chiral sulfur compounds SO(X)(Me) (X = Cl, OMe, p-MePh) has been carried out by means of the DFT(Becke3LYP) method. Our results reveal that in the case of X = Cl, an organic tertiary amine such as NMe3 can catalyze the racemization. The base-catalyzed inversion of SO(CI)(Me) is proposed as a feasible dynamic kinetic resolution mechanism for the synthesis of chiral sulfoxides by the DAG method.

Original language	English
Pages (from-to)	2197-2200
Journal	Organic Letters
Volume	6
Issue number	13
DOIs	https://doi.org/10.1021/ol0493507
Publication status	Published - 24 Jun 2004

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title = "Base-catalyzed inversion of chiral sulfur centers. A computational study",

abstract = "A theoretical study on the pyramidal inversion of the chiral sulfur compounds SO(X)(Me) (X = Cl, OMe, p-MePh) has been carried out by means of the DFT(Becke3LYP) method. Our results reveal that in the case of X = Cl, an organic tertiary amine such as NMe3 can catalyze the racemization. The base-catalyzed inversion of SO(CI)(Me) is proposed as a feasible dynamic kinetic resolution mechanism for the synthesis of chiral sulfoxides by the DAG method.",

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AU - Maseras, Feliu

AU - Khiar, Noureddine

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N2 - A theoretical study on the pyramidal inversion of the chiral sulfur compounds SO(X)(Me) (X = Cl, OMe, p-MePh) has been carried out by means of the DFT(Becke3LYP) method. Our results reveal that in the case of X = Cl, an organic tertiary amine such as NMe3 can catalyze the racemization. The base-catalyzed inversion of SO(CI)(Me) is proposed as a feasible dynamic kinetic resolution mechanism for the synthesis of chiral sulfoxides by the DAG method.

AB - A theoretical study on the pyramidal inversion of the chiral sulfur compounds SO(X)(Me) (X = Cl, OMe, p-MePh) has been carried out by means of the DFT(Becke3LYP) method. Our results reveal that in the case of X = Cl, an organic tertiary amine such as NMe3 can catalyze the racemization. The base-catalyzed inversion of SO(CI)(Me) is proposed as a feasible dynamic kinetic resolution mechanism for the synthesis of chiral sulfoxides by the DAG method.

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DO - 10.1021/ol0493507

M3 - Article

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