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

Departament de Química

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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.

Idioma original	Anglès
Pàgines (de-a)	2197-2200
Revista	Organic Letters
Volum	6
Número	13
DOIs	https://doi.org/10.1021/ol0493507
Estat de la publicació	Publicada - 24 de juny 2004

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10.1021/ol0493507

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@article{67074e3053ea4bdcae0f28cb6a349250,

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.",

author = "David Balcells and Feliu Maseras and Noureddine Khiar",

year = "2004",

month = jun,

day = "24",

doi = "10.1021/ol0493507",

language = "English",

volume = "6",

pages = "2197--2200",

number = "13",

}

TY - JOUR

T1 - Base-catalyzed inversion of chiral sulfur centers. A computational study

AU - Balcells, David

AU - Maseras, Feliu

AU - Khiar, Noureddine

PY - 2004/6/24

Y1 - 2004/6/24

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.

U2 - 10.1021/ol0493507

DO - 10.1021/ol0493507

M3 - Article

SN - 1523-7060

VL - 6

SP - 2197

EP - 2200

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

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