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

2018-07-19, Fearraigh, Martin P., Matlock, Johnathan V., Illa, Ona, McGarrigle, Eoghan M., Aggarwal, Varinder K.

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.