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Synfacts 2007(12): 1287-1287
DOI: 10.1055/s-2007-991373
DOI: 10.1055/s-2007-991373
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Copper-Catalyzed Asymmetric N-H Insertions
E. C. Lee, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200712/lookinside/thumbnails/10.1055-s-2007-991373-1.jpg)
Significance
A copper-catalyzed asymmetric insertion of α-diazo esters into the N-H bond of carbamates is described using a chiral bis(oxazoline) ligand. A variety of aryl groups are tolerated as substituents on the diazo ester, and the methodology is described for both Boc- and Cbz-protected amines. The products are valuable α-amino acids and are produced in good yields and enantioselectivities. A competition study shows that N-H insertion is preferred over N-D insertion.