Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

J Am Chem Soc. 2006 Sep 13;128(36):11776-7. doi: 10.1021/ja064858l.

Abstract

A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Alcohols / isolation & purification*
  • Hydrogen / chemistry
  • Ketones / chemistry
  • Lanthanum / chemistry*
  • Lithium / chemistry*
  • Naphthols / chemistry
  • Nitro Compounds / chemistry
  • Nitro Compounds / isolation & purification*
  • Oxidation-Reduction
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Alcohols
  • BINOL, naphthol
  • Ketones
  • Naphthols
  • Nitro Compounds
  • Lanthanum
  • Hydrogen
  • Lithium