Stereoselective Synthesis of γ-Lactams from Imines and Cyanosuccinic Anhydrides

Stereoselective Synthesis of γ-Lactams from Imines and Cyanosuccinic Anhydrides

Abstract : A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization, thus providing access to enantiomerically pure penta-substituted lactam products.

Tan, D. Q.; Younai, A.; Pattawong, O.; Fettinger, J. C.; Cheong, P. H.-Y.; Shaw, J. T. Org. Lett. 2013, Article ASAP. DOI: 10.1021/ol402554n