Enantioselective synthesis of beta-(3-hydroxypyrazol-1-yl) ketones using an organocatalyzed Michael addition reaction

Org Lett. 2009 Jun 4;11(11):2249-52. doi: 10.1021/ol900538q.

Abstract

Beta-(3-hydroxypyrazol-1-yl) ketones have been prepared in high yields and excellent enantioselectivities (94-98% ee) via a Michael addition reaction between 2-pyrazolin-5-ones and aliphatic acyclic alpha,beta-unsaturated ketones using 9-epi-9-amino-9-deoxyquinine as the catalyst. These results account for the first example of an aza-Michael addition of the ambident 2-pyrazolin-5-one anion to a Michael acceptor.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoic Acid / chemistry
  • Catalysis
  • Cyclization
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Pyrazolones / chemistry*
  • Stereoisomerism

Substances

  • Ketones
  • Pyrazolones
  • Benzoic Acid