Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis

J Am Chem Soc. 2009 Apr 8;131(13):4572-3. doi: 10.1021/ja809723u.

Abstract

Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.

Publication types

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

MeSH terms

  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry*
  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Catalysis
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry*
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • Alkenes
  • Lactones
  • Nitro Compounds
  • Zinc
  • 4-Butyrolactone