A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes

J Am Chem Soc. 2015 Nov 4;137(43):13760-3. doi: 10.1021/jacs.5b09146. Epub 2015 Oct 22.

Abstract

A cooperative Cu/Pd-catalyzed asymmetric three-component reaction of styrenes, B2(pin)2, and allyl carbonates was reported. This reaction, in the presence of chiral CuOAc/SOP and achiral Pd(dppf)Cl2 catalysts, occurs smoothly with high enantioselectivities (up to 97% ee) . The allylboration products, which contain alkene (or diene) unite and alkylboron group, are easily functionalized. The utility of this protocol was demonstrated through the synthesis of an antipsychotic drug, (-)-preclamol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Allyl Compounds / chemical synthesis*
  • Allyl Compounds / chemistry
  • Boranes / chemical synthesis*
  • Boranes / chemistry
  • Catalysis
  • Copper / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Allyl Compounds
  • Boranes
  • Organometallic Compounds
  • Piperidines
  • Palladium
  • Copper
  • preclamol