BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination

J Org Chem. 2012 Sep 21;77(18):7932-44. doi: 10.1021/jo301064u. Epub 2012 Sep 4.

Abstract

A five-component catalyst assembly/aziridination reaction is described starting from an aldehyde, an amine, ethyl diazoacetate, B(OPh)(3), and a molecule of a vaulted biaryl ligand (VAPOL or VANOL). A remarkable level of chemo-selectivity was observed since, while 10 different products could have resulted from various reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only two other products could be detected in 3% yield. Studies reveal that the first in a sequence of three reactions is an exceedingly rapid amine-induced assembly of an amino-BOROX chiral Brønsted acid species from VAPOL and B(OPh)(3), which is followed by imine formation from the amine and aldehyde and the concomitant formation of an imino-BOROX chiral Brønsted acid and finally the reaction of the imine with ethyl diazoacetate mediated by the imino-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemistry*
  • Amines / chemistry*
  • Aziridines / chemistry*
  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry*
  • Catalysis
  • Imines / chemistry*
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amines
  • Aziridines
  • Boron Compounds
  • Imines
  • Ligands
  • Organometallic Compounds
  • aziridine