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.

SUBMITTER: Tan DQ 

PROVIDER: S-EPMC3874237 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature