Role of reversible dimerization in reactions of amphoteric aziridine aldehydes

J Org Chem. 2012 Jul 6;77(13):5613-23. doi: 10.1021/jo3007418. Epub 2012 Jun 14.

Abstract

Unprotected aziridine aldehydes belong to the amphoteric class of molecules by virtue of their dual nucleophilicity/electrophilicity. The dimeric nature of these molecules, brought together by a weak and reversible aminal "connection", was found to be an important element of reactivity control. We present evidence that reversible dimer dissociation is instrumental in aziridine aldehyde transformations. We anticipate further developments that will unveil other synthetic consequences of remote control of selectivity through forging reversible covalent interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Dimerization
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Aldehydes
  • Aziridines