Enediyne-Comprising Amino Aldehydes in the Passerini Reaction

ACS Comb Sci. 2018 Mar 12;20(3):151-155. doi: 10.1021/acscombsci.7b00167. Epub 2018 Jan 30.

Abstract

Multicomponent reactions represent a highly efficient approach to a broad spectrum of structurally diverse compounds starting from simple and affordable compounds. A focused library of tweezers-like compounds is prepared by employing the multicomponent Passerini reaction comprising enediyne-derived amino aldehydes. The reaction proceeds under mild conditions yielding Passerini products in good to excellent yields. Postcondensation modifications of Passerini products are demonstrated through a simple deprotection/coupling approach comprising amino functionality, furnishing enediyne cores with highly decorated arms.

Keywords: Passerini reaction; enediynes; multicomponent reactions; receptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Combinatorial Chemistry Techniques / methods
  • Enediynes / chemical synthesis*
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Molecular Structure
  • Small Molecule Libraries / chemical synthesis*

Substances

  • Aldehydes
  • Enediynes
  • Small Molecule Libraries