The asymmetric total synthesis of the new non-natural 1β-methoxycarbapenem (1) has been achieved via highly diastereoselective alkylation at the C-4 position of 4-acetoxyazetidin-2-one (4) with the tin enolate of thiazolidinethione (3); the stereochemistry has been confirmed by an X-ray crystal structure determination of the derivative (13).
Y. Nagao, T. Abe, H. Shimizu, T. Kumagai and Y. Inoue, J. Chem. Soc., Chem. Commun., 1989, 821 DOI: 10.1039/C39890000821
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