Reaction of silylimines with ester enolates. Synthesis of N-unsubstituted azetidinones starting from nitriles
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 945-948
- https://doi.org/10.1039/p19880000945
Abstract
The reduction of aromatic, vinylic, and aliphatic nitriles with several ‘metal–aluminium hydrides’ produces an addition product which is readily converted to a β-lactam derivative by treatment with Me3SiCl followed by the addition of lithium ester enolates. The factors influencing the course of the cycloaddition-type reaction are discussed. A relatively simple synthetic procedure for the preparation of N-unsubstituted azetidin-2-ones in satisfactory yields is reported.This publication has 2 references indexed in Scilit:
- A convenient synthesis of 4-unsubstituted .beta.-lactamsJournal of the American Chemical Society, 1985
- N-Trimethylsilylimines: applications to the syntheses of .beta.-lactamsJournal of the American Chemical Society, 1984