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Generation and hydrolysis of N -acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2020-06-02 , DOI: 10.1007/s10593-020-02707-3
R. Alan Aitken , Alexandra M. Z. Slawin , Andrew Wilson

In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterized, but alkaline treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by X-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 2-amino alcohols.


中文翻译:

N-酰基恶唑啉鎓盐的生成和水解可实现手性氨基醇的区域特异性酰化

为了形成2-亚烷基-1,3-恶唑烷,手性2-恶唑啉已被N-烷基化和N-酰化。已经制备并表征了两种新的N-甲基恶唑啉鎓盐,但是碱处理导致它们分解。相反,尝试分离出三种N-苯甲酰恶唑啉鎓盐会产生其环水解的产物:一种是通过X射线衍射证实其结构的不对称二酰化氨基醇。总之,该方法允许2-氨基醇的逐步区域特异性的NO-二酰化。
更新日期:2020-06-02
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