通过侧链氨基磺酸酯实现氮杂环丙烷的开环反应，可用于区域选择性和立体特异性地制备邻二胺。
Ring Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparation of Vicinal Diamines.
作者信息
Nagamalla Someshwar, Thomas Annu Anna, Nirpal Appasaheb K, Mague Joel T, Sathyamoorthi Shyam
机构信息
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, United States.
出版信息
J Org Chem. 2023 Nov 17;88(22):15989-16006. doi: 10.1021/acs.joc.3c01731. Epub 2023 Oct 30.
Abstract
The ring opening of aziridines by pendant sulfamates is a viable strategy for the rapid preparation of vicinal diamines. Our reaction is compatible with both disubstituted - and -aziridines; unsubstituted, -alkyl, and -aryl sulfamates engage effectively. In all cases examined, the cyclization reaction is perfectly regioselective and stereospecific. Once activated, the product oxathiazinane heterocycles can be ring opened with a diverse range of nucleophiles.
摘要
通过侧链氨基磺酸酯使氮丙啶开环是快速制备邻二胺的可行策略。我们的反应与二取代氮丙啶和氮丙啶均兼容；未取代的、烷基和芳基氨基磺酸酯均能有效参与反应。在所研究的所有情况下，环化反应具有完美的区域选择性和立体专一性。一旦被激活，产物氧杂噻嗪烷杂环可以被多种亲核试剂开环。
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