Synthesis of Isothiocineole and Application in Multi-gram Scale Sulfur Ylide-mediated Asymmetric Epoxidation and Aziridination

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Title: Synthesis of Isothiocineole and Application in Multi-gram Scale Sulfur Ylide-mediated Asymmetric Epoxidation and Aziridination
Authors: Fearraigh, Martin P.
Matlock, Johnathan V.
Illa, Ona
McGarrigle, Eoghan M.
Aggarwal, Varinder K.
Permanent link: http://hdl.handle.net/10197/10398
Date: 19-Jul-2018
Online since: 2019-05-13T08:29:41Z
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.
Funding Details: Irish Research Council
Science Foundation Ireland
Type of material: Journal Article
Publisher: Thieme
Journal: Synthesis
Volume: 50
Issue: 17
Start page: 3337
End page: 3343
Copyright (published version): 2018 Thieme Publishing Group
Keywords: Sulfur ylideAsymmetric epoxidationAsymmetric aziridinationChiral sulfide
DOI: 10.1055/s-0037-1609580
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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