Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation

Pádraig Kelly; Simon E. Lawrence; Anita R. Maguire

doi:10.1002/ejoc.200600320

Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation

University College Cork

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Abstract

Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail.

Original language	English
Pages (from-to)	4500-4509
Number of pages	10
Journal	European Journal of Organic Chemistry
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.200600320
Publication status	Published - 25 Sep 2006

Keywords

Asymmetric catalysis
Enantioselectivity
Kinetic resolution
Oxidation
Sulfoxides

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10.1002/ejoc.200600320

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title = "Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation",

abstract = "Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90\% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail.",

keywords = "Asymmetric catalysis, Enantioselectivity, Kinetic resolution, Oxidation, Sulfoxides",

author = "P{\'a}draig Kelly and Lawrence, \{Simon E.\} and Maguire, \{Anita R.\}",

year = "2006",

month = sep,

day = "25",

doi = "10.1002/ejoc.200600320",

language = "English",

pages = "4500--4509",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "19",

}

Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation. / Kelly, Pádraig; Lawrence, Simon E.; Maguire, Anita R.
In: European Journal of Organic Chemistry, No. 19, 25.09.2006, p. 4500-4509.

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

TY - JOUR

T1 - Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation

T2 - A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation

AU - Kelly, Pádraig

AU - Lawrence, Simon E.

AU - Maguire, Anita R.

PY - 2006/9/25

Y1 - 2006/9/25

N2 - Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail.

AB - Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail.

KW - Asymmetric catalysis

KW - Enantioselectivity

KW - Kinetic resolution

KW - Oxidation

KW - Sulfoxides

UR - https://www.scopus.com/pages/publications/33749452984

U2 - 10.1002/ejoc.200600320

DO - 10.1002/ejoc.200600320

M3 - Article

AN - SCOPUS:33749452984

SN - 1434-193X

SP - 4500

EP - 4509

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19

ER -

Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation

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Keywords

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