Boroalkyl group migration provides a versatile entry into α-aminoboronic acid derivatives

J Am Chem Soc. 2012 Jun 20;134(24):9926-9. doi: 10.1021/ja304173d. Epub 2012 Jun 8.

Abstract

A reaction exemplifying migration of boron-substituted carbon is described. We show that α-boroalkyl groups of transient boroalkyl acyl azide intermediates readily migrate from carbon to nitrogen. This process allows access to a new class of stable molecules, α-boryl isocyanates, from α-borylcarboxylic acid precursors. The methodology facilitates synthesis of a wide range of α-aminoboronic acid derivatives, including α,α-disubstituted analogues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry*
  • Azides / chemistry
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Carbon / chemistry
  • Isocyanates / chemical synthesis
  • Isocyanates / chemistry

Substances

  • Amino Acids
  • Azides
  • Boron Compounds
  • Boronic Acids
  • Isocyanates
  • Carbon