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

18 Citations (Scopus)

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

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Lactams
Imines
Anhydrides
anhydrides
imines
synthesis
Rubiaceae
Temperature
room temperature
products

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

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

Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides. / Tan, Darlene Q.; Younai, Ashkaan; Pattawong, Ommidala; Fettinger, James C.; Cheong, Paul Ha Yeon; Shaw, Jared T.

In: Organic Letters, Vol. 15, No. 19, 04.10.2013, p. 5126-5129.

Research output: Contribution to journalArticle

Tan, DQ, Younai, A, Pattawong, O, Fettinger, JC, Cheong, PHY & Shaw, JT 2013, 'Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides', Organic Letters, vol. 15, no. 19, pp. 5126-5129. https://doi.org/10.1021/ol402554n
Tan DQ, Younai A, Pattawong O, Fettinger JC, Cheong PHY, Shaw JT. Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides. Organic Letters. 2013 Oct 4;15(19):5126-5129. https://doi.org/10.1021/ol402554n
Tan, Darlene Q. ; Younai, Ashkaan ; Pattawong, Ommidala ; Fettinger, James C. ; Cheong, Paul Ha Yeon ; Shaw, Jared T. / Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides. In: Organic Letters. 2013 ; Vol. 15, No. 19. pp. 5126-5129.
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