β-Lactam Synthesis by Ugi Reaction of β-Keto Acids in Aqueous Solution

Abstract

A novel protocol for accelerating Ugi reactions in aqueous solution enables the application of the reaction to β-keto acids. This process results in the preparation of even highly strained ring-fused β-lactams.

Key words

solvent effects - green chemistry - combinatorial chemistry - multicomponent reactions - condensation

References

• 1 Pirrung MC. Sarma KD. J. Am. Chem. Soc.  2004,  126:  444 
• 2a Breslow R. Acc. Chem. Res.  1991,  24:  159 
• 2b Otto S. Engberts JBFN. Org. Biomol. Chem.  2003,  1:  2809 
• 3 Chandrasekhar J. Shariffskul S. Jorgensen WL. J. Phys. Chem. B  2002,  106:  8078 
• 4a Lubineau A. Augé J. Top. Curr. Chem.  1999,  206:  2 
• 4b Lubineau A. Augé J. Queneau Y. Synthesis  1994,  742 
• 5 Lubineau A. J. Org. Chem.  1986,  51:  2142 
• 6 Gedey S. van der Eycken J. Fülöp F. Org. Lett.  2002,  4:  1967 
• 7a Hanusch-Kompa C. Ugi I. Tetrahedron Lett.  1998,  39:  2725 
• 7b Short KM. Ching BW. Mjjali AMM. Tetrahedron  1997,  53:  6653 
• 7c Harriman GCB. Tetrahedron Lett.  1997,  38:  5591 
• 8 Jenner G. Tetrahedron Lett.  2002,  43:  1235