Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides

Darlene Q. Tan, Ashkaan Younai, Ommidala Pattawong, James C. Fettinger, Paul Ha Yeon Cheong, Jared T. Shaw

Research output: Contribution to journalArticle

20 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)5126-5129
Number of pages4
JournalOrganic Letters
Volume15
Issue number19
DOIs
StatePublished - Oct 4 2013

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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    Tan, D. Q., Younai, A., Pattawong, O., Fettinger, J. C., Cheong, P. H. Y., & Shaw, J. T. (2013). Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides. Organic Letters, 15(19), 5126-5129. https://doi.org/10.1021/ol402554n