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

Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination
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DOI:
10.1055/s-0037-1609580
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发表时间:
2018-09-01
影响因子:
2.6
通讯作者:
Aggarwal, Varinder K.
Aggarwal, Varinder K.
中科院分区:
化学4区
文献类型:
--
作者:
Fearraigh, Martin P. O.;Matlock, Johnathan, V;Aggarwal, Varinder K.

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描述了由柠檬烯和元素硫以多克规模合成手性硫化物异硫辛烯脑及其烷基化以制备>50 g相应的苄基锍盐。该盐的应用硫叶立德介导的醛的不对称环氧化和亚胺的不对称氮杂环丙烷化在>5克的规模进行了演示。
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.