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Synthesis 2018; 50(17): 3337-3343
DOI: 10.1055/s-0037-1609580
DOI: 10.1055/s-0037-1609580
psp
Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination
Authors
This 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).fundi
Weitere Informationen
Publikationsverlauf
Received: 18. Juni 2018
Accepted: 21. Juni 2018
Publikationsdatum:
19. Juli 2018 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609580.
- Supporting Information (PDF)
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 (ZIP)
-
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