Ammonia synthons for the multicomponent assembly of complex γ-lactams

Darlene Q. Tan, Kevin S. Martin, James C. Fettinger, Jared T. Shaw

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.

Original languageEnglish (US)
Pages (from-to)6781-6786
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume108
Issue number17
DOIs
StatePublished - Apr 26 2011

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Lactams
Ammonia
Nitrogen
X-Rays

Keywords

  • Multicomponent reaction
  • Stereoselective

ASJC Scopus subject areas

  • General

Cite this

Ammonia synthons for the multicomponent assembly of complex γ-lactams. / Tan, Darlene Q.; Martin, Kevin S.; Fettinger, James C.; Shaw, Jared T.

In: Proceedings of the National Academy of Sciences of the United States of America, Vol. 108, No. 17, 26.04.2011, p. 6781-6786.

Research output: Contribution to journalArticle

Tan, Darlene Q. ; Martin, Kevin S. ; Fettinger, James C. ; Shaw, Jared T. / Ammonia synthons for the multicomponent assembly of complex γ-lactams. In: Proceedings of the National Academy of Sciences of the United States of America. 2011 ; Vol. 108, No. 17. pp. 6781-6786.
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