Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols
Abstract
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 characterised but base 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 1,2-amino alcohols.
Citation
Aitken , R A , Slawin , A M Z & Wilson , A 2020 , ' Generation and hydrolysis of N -acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols ' , Chemistry of Heterocyclic Compounds , vol. 56 , no. 5 , pp. 611-614 . https://doi.org/10.1007/s10593-020-02707-3
Publication
Chemistry of Heterocyclic Compounds
Status
Peer reviewed
ISSN
1573-8353Type
Journal article
Rights
Copyright © 2020 Springer Science+Business Media, LLC. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1007/s10593-020-02707-3
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