Repozytorium publikacji - Politechnika Gdańska

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Repozytorium publikacji
Politechniki Gdańskiej

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A new approach to the stereoselective synthesis of trans-3-carbamoyl-b-lactam moieties†

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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