Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines

Chem Commun (Camb). 2015 Nov 4;51(85):15588-91. doi: 10.1039/c5cc06323j.

Abstract

The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry of this class of four-membered heterocycles. Two unexpected and unprecedented results have been observed: an "ortho-effect" accounting for the regioselective functionalization of the azetidine ring, and self-condensation leading to new and interesting azetidine-based peptidomimetics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azetidines / chemical synthesis*
  • Azetidines / chemistry
  • Molecular Structure
  • Peptidomimetics / chemical synthesis*
  • Peptidomimetics / chemistry
  • Stereoisomerism

Substances

  • Azetidines
  • Peptidomimetics