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Synthesis 2018; 50(17): 3337-3343
DOI: 10.1055/s-0037-1609580
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© Georg Thieme Verlag Stuttgart · New York

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

Martin P. Ó Fearraigh
a   Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland   Email: eoghan.mcgarrigle@ucd.ie
,
Johnathan V. Matlock
b   School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
,
Ona Illa
b   School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
c   Departament de Química, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Spain
,
Eoghan M. McGarrigle  *
a   Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland   Email: eoghan.mcgarrigle@ucd.ie
b   School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
,
Varinder K. Aggarwal*
b   School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
› Author AffiliationsThis publication is based on work supported by the University of Bristol, the Irish Research Council (GOIPG/2014/528), Science Foundation Ireland, and the Marie-Curie Action COFUND (11/SIRG/B2154).
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Further Information

Publication History

Received: 18 June 2018

Accepted: 21 June 2018

Publication Date:
19 July 2018 (online)

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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.

Key words

sulfur ylide - asymmetric epoxidation - asymmetric aziridination - chiral sulfide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609580.
  • Supporting Information

Primary Data

    for this article are available online at https://doi.org/10.1055/s-0037-1609580 and can be cited using the following DOI: 10.4125/pd0099th.
  • Primary Data
 

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