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

Author(s)
Fearraigh, Martin P.  
Matlock, Johnathan V.  
Illa, Ona  
McGarrigle, Eoghan M.  
Aggarwal, Varinder K.  
Uri
http://hdl.handle.net/10197/10398
Date Issued
2018-07-19
Date Available
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.
Sponsorship
Irish Research Council
Science Foundation Ireland
Other Sponsorship
University of Bristol
Marie-Curie Action COFUND
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
Subjects

Sulfur ylide

Asymmetric epoxidatio...

Asymmetric aziridinat...

Chiral sulfide

DOI
10.1055/s-0037-1609580
Language
English
Status of Item
Peer reviewed
ISSN
0039-7881
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by-nc-nd/3.0/ie/
File(s)
No Thumbnail Available
Name

SYNTHESIS 2018 McGarrigle Aggarwal for repository upload.pdf

Size

1.74 MB

Format

Adobe PDF

Checksum (MD5)

472d7ea23fa6f6a17f65a55f8c2cfd02

Owning collection
Chemistry Research Collection

Item descriptive metadata is released under a CC-0 (public domain) license: https://creativecommons.org/public-domain/cc0/.
All other content is subject to copyright.

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