Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides
- Author(s): Tan, DQ
- Younai, A
- Pattawong, O
- Fettinger, JC
- Cheong, PHY
- Shaw, JT
- et al.
Published Web Locationhttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC3874237/pdf/nihms528048.pdf
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. © 2013 American Chemical Society.
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