Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols
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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.
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
Chemistry of Heterocyclic Compounds
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