Rh(I)/Sc(OTf)3-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones

Mol Divers. 2019 Nov;23(4):997-1010. doi: 10.1007/s11030-019-09941-8. Epub 2019 Apr 5.

Abstract

A Rh(I)/Sc(III) co-catalyzed synthesis of highly valuable functionalized 1,4-diketone derivatives in good yields and with an excellent diastereoselectivity. The established method provides a rapid approach to structurally diverse 1,4-diketone scaffold in a very mild and rapid fashion from simple starting materials. Moreover, the protocol could be easily scaled up to gram-scale synthesis. An attempt to develop an asymmetric version of the Rh(I)/guanidine system was also explored, resulting in a moderate enantioselectivity (71% ee).

Keywords: 1,4-diketone structural diversity; Ammonium ylide; Rh(I)/Sc(III) co-catalyzed; Three-component reaction.

MeSH terms

  • Ammonium Compounds / chemistry
  • Aniline Compounds / chemistry
  • Catalysis
  • Indoles / chemistry
  • Ketones / chemistry*
  • Rhodium / chemistry*
  • Scandium / chemistry*

Substances

  • Ammonium Compounds
  • Aniline Compounds
  • Indoles
  • Ketones
  • Rhodium
  • Scandium