Enantioselective Staudinger Synthesis of β-Lactams Catalyzed by a Planar-Chiral Nucleophile
Brian L. Hodous and Gregory C. Fu*
*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: gcfmit.edu
B. L. Hodous, G. C. Fu, J. Am. Chem. Soc., 2002, 124, 1578-1579.
DOI: 10.1021/ja012427r (free Supporting Information)
The Staudinger synthesis, an overall [2 + 2] cycloaddition of a ketene with an imine, provides a nicely convergent route to biologically and synthetically interesting β-lactams. A planar-chiral derivative of 4-(pyrrolidino)pyridine serves as a very effective enantioselective catalyst coupling a range of symmetrical and unsymmetrical ketenes with various imines with very good stereoselection and yield.
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E. C. Lee, B. L. Hodous, E. Bergin, C. Shih, G. C. Fu, J. Am. Chem. Soc., 2005, 127, 11586-11587.