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Preparation of Sulfilimines by Sulfur-Alkylation of N-Acyl Sulfenamides with Alkyl Halides
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2023-05-23 , DOI: 10.1021/acs.joc.3c00750
Andrew T Champlin 1 , Jonathan A Ellman 1
Affiliation  

Sulfur alkylation of N-acyl sulfenamides with alkyl halides provides sulfilimines in 47% to 98% yields. A broad scope was established with a variety of aryl and alkyl sulfenamides, including for different N-acyl groups. Alkyl halides with different steric and electronic properties were effective inputs, including methyl, primary, secondary, benzyl, and propargyl halides. A proof-of-concept asymmetric phase-transfer alkylation was also demonstrated. A sulfilimine product was readily converted to an N-acyl and to a free sulfoximine, which represent important motifs in medicinal chemistry.

中文翻译:

N-酰基次磺酰胺与烷基卤化物的硫烷基化制备硫亚胺

N-酰基亚磺酰胺与烷基卤化物的硫烷基化以 47% 至 98% 的收率提供硫亚胺。使用各种芳基和烷基亚磺酰胺建立了广泛的范围,包括不同的N-酰基。具有不同空间和电子特性的烷基卤化物是有效的输入,包括甲基、伯、仲、苄基和炔丙基卤化物。还展示了概念验证不对称相转移烷基化。硫亚胺产物很容易转化为N-酰基和游离亚砜亚胺,这代表了药物化学中的重要基序。
更新日期:2023-05-23
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