Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos

J Org Chem. 2012 Apr 20;77(8):4143-7. doi: 10.1021/jo3002535. Epub 2012 Apr 10.

Abstract

A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates / chemistry*
  • Catalysis
  • Cyclization
  • Isatin / chemical synthesis*
  • Isatin / chemistry*
  • Maleimides / chemical synthesis*
  • Maleimides / chemistry*
  • Molecular Structure
  • Phosphines / chemistry*
  • Stereoisomerism

Substances

  • Carbonates
  • Maleimides
  • Phosphines
  • Isatin
  • N-phenylmaleimide