Catalytic asymmetric synthesis of 2,2-disubstituted oxetanes from ketones by using a one-pot sequential addition of sulfur ylide

Angew Chem Int Ed Engl. 2009;48(9):1677-80. doi: 10.1002/anie.200805473.

Abstract

Better the second time around: The title compounds were synthesized by using a one-pot double methylene transfer catalyzed by a heterobimetallic La/Li complex. Chiral amplification in the second step was the key to obtaining oxetanes in high enantiomeric excess (see scheme).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Ketones / chemistry*
  • Metals, Rare Earth / chemistry
  • Organophosphorus Compounds / chemistry
  • Stereoisomerism
  • Sulfur / chemistry*

Substances

  • Ethers, Cyclic
  • Ketones
  • Metals, Rare Earth
  • Organophosphorus Compounds
  • Sulfur
  • oxetane