A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties?
New Journal of Chemistry Pub Date: 2017-02-15 DOI: 10.1039/C7NJ00445A
Abstract
One-pot synthesis of optically active 1,4-disubstituted-3-carbamoyl-azetidinones from 5-[(N-arylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines is achieved via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition. Three possible chiral induction approaches were tested and (R)-(+)-1-phenylethylamine was confirmed as the best chiral auxiliary. Among the four possible diastereoisomers, only two with significant excess of one were formed.
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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