Iodine(III)-Catalyzed Cascade Reactions Enabling a Direct Access to β-Lactams and α-Hydroxy-β-amino Acids.

Org Lett

Department of Chemistry and Catalysis Research Center (CRC), Technical University of Munich, Lichtenbergstrasse 4, 85747 Garching, Germany.

Published: July 2016

In the presented method, a one-pot metal-free access to β-lactams is provided. The developed strategy employs a hypervalent iodine(III)-triggered bromination/rearrangement/cyclization cascade reaction that allows the straightforward synthesis of a broad range of structurally different lactams from cheap and easily available imides. This triple cascade reaction is furthermore extendable by an in situ ring-opening reaction, giving direct access to isoserine derivatives from simple imines in a four-step, one-pot reaction.

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http://dx.doi.org/10.1021/acs.orglett.6b01658DOI Listing

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