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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 Location

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3874237/pdf/nihms528048.pdf
No data is associated with this publication.
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. © 2013 American Chemical Society.

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