A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H

Org Biomol Chem. 2015 Nov 14;13(42):10456-60. doi: 10.1039/c5ob01838b. Epub 2015 Sep 30.

Abstract

N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Amino Acids / chemistry*
  • Imidazoles / chemistry*
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Time Factors

Substances

  • Aldehydes
  • Amino Acids
  • Imidazoles
  • Organometallic Compounds
  • N,N-carbonyldiimidazole
  • diisobutylaluminum