Asymmetric Ni(II)/Cr(II)-mediated coupling reaction: stoichiometric process

Org Lett. 2002 Dec 12;4(25):4431-4. doi: 10.1021/ol0269805.

Abstract

[reaction: see text] Via an X-ray analysis, the sulfonamide bearing R(1) = i-Pr, R(2) = Me, and R(3) = Me is shown to be a tridentate ligand to a Cr(III) salt. This class of ligands, represented by R(1) = t-Bu, R(2) = 2-naphthyl, and R(3) = Me, is effective to achieve an asymmetric Ni/Cr-mediated coupling reaction and, with the C14-C38 segment of halichondrins, its synthetic potential has been demonstrated. A possible mechanism is suggested for the process.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Chromium / chemistry*
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry*
  • Ligands
  • Macrolides
  • Molecular Conformation
  • Molecular Structure
  • Nickel / chemistry*
  • Stereoisomerism

Substances

  • Ethers, Cyclic
  • Ligands
  • Macrolides
  • Chromium
  • halichondrin B
  • Nickel