Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination

Martin Fearraigh; Johnathan Matlock; Ona Illa Soler; Eoghan M. McGarrigle; Varinder Aggarwal

doi:10.1055/s-0037-1609580

Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination

Martin Fearraigh, Johnathan Matlock, Ona Illa Soler, Eoghan M. McGarrigle, Varinder Aggarwal

School of Chemistry

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Abstract

The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.

Original language	English
Pages (from-to)	3337-3343
Number of pages	7
Journal	Synthesis (Germany)
Volume	50
Issue number	17
Early online date	19 Jul 2018
DOIs	https://doi.org/10.1055/s-0037-1609580
Publication status	Published - 1 Sept 2018

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This is the accepted author manuscript (AAM). The final published version (version of record) is available online via Georg Thieme Verlag at DOI: 10.1055/s-0037-1609580. Please refer to any applicable terms of use of the publisher.
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title = "Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination",

abstract = "The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.",

author = "Martin Fearraigh and Johnathan Matlock and {Illa Soler}, Ona and McGarrigle, {Eoghan M.} and Varinder Aggarwal",

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T1 - Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination

AU - Fearraigh, Martin

AU - Matlock, Johnathan

AU - Illa Soler, Ona

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder

PY - 2018/9/1

Y1 - 2018/9/1

N2 - The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.

AB - The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.

U2 - 10.1055/s-0037-1609580

DO - 10.1055/s-0037-1609580

M3 - Article (Academic Journal)

SN - 0039-7881

VL - 50

SP - 3337

EP - 3343

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 17

ER -

Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination

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