Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts

Org Lett. 2011 Oct 21;13(20):5556-9. doi: 10.1021/ol202276h. Epub 2011 Sep 14.


An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd(II) complex or strong Brønsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aza Compounds / chemistry*
  • Carbamates / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Palladium / chemistry
  • Stereoisomerism


  • Aza Compounds
  • Carbamates
  • Ketones
  • Palladium