Enantioselective synthesis of cyclopropanes that contain fluorinated tertiary stereogenic carbon centers: a chiral α-fluoro carbanion strategy

Angew Chem Int Ed Engl. 2012 Jul 9;51(28):6966-70. doi: 10.1002/anie.201202451. Epub 2012 Jun 11.

Abstract

Chiral transfer: the fluorinated sulfoximine (see scheme; Ts=p-toluenesulfonyl) was synthesized and used as the first chiral fluoromethylenation reagent for the synthesis of cyclopropanes that contain fluorinated tertiary stereogenic carbon centers in good yields, good diastereoselectivity, and excellent enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Cyclopropanes / chemical synthesis*
  • Halogenation
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism

Substances

  • Anions
  • Cyclopropanes
  • Hydrocarbons, Fluorinated
  • Carbon