Influence of chiral thiols on the diastereoselective synthesis of γ-lactams from cyclic anhydrides

Ashkaan Younai, James C. Fettinger, Jared T. Shaw

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The synthesis of γ-lactams from both four-component and imine-anhydride reactions is reported. The synthesis of 2-phenylcyclohexanethiol is described and this compound was evaluated along with an additional seven chiral thiols. A range of selectivity and yields was observed and comparisons to established reactions are made in order to account for the observed reactivity.

Original languageEnglish (US)
Pages (from-to)4320-4327
Number of pages8
JournalTetrahedron
Volume68
Issue number22
DOIs
StatePublished - Jun 3 2012

Fingerprint

Lactams
Imines
Anhydrides
Sulfhydryl Compounds

Keywords

  • Chiral auxiliary
  • Lactam
  • Multi-component reaction
  • Thiol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Influence of chiral thiols on the diastereoselective synthesis of γ-lactams from cyclic anhydrides. / Younai, Ashkaan; Fettinger, James C.; Shaw, Jared T.

In: Tetrahedron, Vol. 68, No. 22, 03.06.2012, p. 4320-4327.

Research output: Contribution to journalArticle

Younai, Ashkaan ; Fettinger, James C. ; Shaw, Jared T. / Influence of chiral thiols on the diastereoselective synthesis of γ-lactams from cyclic anhydrides. In: Tetrahedron. 2012 ; Vol. 68, No. 22. pp. 4320-4327.
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