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

Martin P.Ó. Fearraigh; Johnathan V. Matlock; Ona Illa; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1055/s-0037-1609580

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

Martin P.Ó. Fearraigh, Johnathan V. Matlock, Ona Illa, Eoghan M. McGarrigle, Varinder K. Aggarwal

Department of Chemistry

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

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Abstract

© 2018 Georg Thieme Verlag KG Stuttgart · New York. 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
Article number	ss-2018-z0422-psp
Pages (from-to)	3337-3343
Journal	Synthesis
Volume	50
Issue number	17
DOIs	https://doi.org/10.1055/s-0037-1609580
Publication status	Published - 1 Jan 2018

Keywords

asymmetric aziridination
asymmetric epoxidation
chiral sulfide
sulfur ylide

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10.1055/s-0037-1609580

https://ddd.uab.cat/record/274097

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title = "Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination",

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keywords = "asymmetric aziridination, asymmetric epoxidation, chiral sulfide, sulfur ylide",

author = "Fearraigh, {Martin P.{\'O}.} and Matlock, {Johnathan V.} and Ona Illa and McGarrigle, {Eoghan M.} and Aggarwal, {Varinder K.}",

year = "2018",

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doi = "10.1055/s-0037-1609580",

language = "English",

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

AU - Fearraigh, Martin P.Ó.

AU - Matlock, Johnathan V.

AU - Illa, Ona

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - © 2018 Georg Thieme Verlag KG Stuttgart · New York. 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 - © 2018 Georg Thieme Verlag KG Stuttgart · New York. 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.

KW - asymmetric aziridination

KW - asymmetric epoxidation

KW - chiral sulfide

KW - sulfur ylide

U2 - 10.1055/s-0037-1609580

DO - 10.1055/s-0037-1609580

M3 - Article

SN - 0039-7881

VL - 50

SP - 3337

EP - 3343

JO - Synthesis

JF - Synthesis

IS - 17

M1 - ss-2018-z0422-psp

ER -

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

Abstract

Keywords

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