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异硫脲催化的磺酰胺的非对映选择性 N-酰化反应。

Isothiourea-Catalyzed Atroposelective N-Acylation of Sulfonamides.

机构信息

NUS Graduate School for Integrative Sciences & Engineering (NGS), National University of Singapore, 21 Lower Kent Ridge, Republic of Singapore 119077.

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Republic of Singapore 117543.

出版信息

Org Lett. 2020 Aug 21;22(16):6447-6451. doi: 10.1021/acs.orglett.0c02266. Epub 2020 Aug 11.

Abstract

We report herein an atroposelective N-acylation of sulfonamides using a commercially available isothiourea catalyst, ()-HBTM, with a simple procedure. The -sulfonyl anilide products can be obtained in good to high enantiopurity, which represents a new axially chiral scaffold. The application of the product as a chiral iodine catalyst is also demonstrated for the asymmetric α-oxytosylation of propiophenone.

摘要

我们在此报告了一种使用市售的异硫脲催化剂()-HBTM 进行的对映选择性 N-酰化磺酰胺的方法,该方法具有简单的操作步骤。 -磺酰基苯胺产物可以以良好到高的对映纯度获得,这代表了一种新的轴向手性支架。还展示了产物作为手性碘催化剂在丙酰苯酮的不对称α-氧代酯化反应中的应用。

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