Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids

Org Lett. 2006 Jul 20;8(15):3371-4. doi: 10.1021/ol061304e.

Abstract

[Structure: see text] Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemistry
  • Aziridines / chemistry*
  • Carboxylic Acids / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amino Alcohols
  • Aziridines
  • Carboxylic Acids
  • Heterocyclic Compounds