Synthesis and Use of Bicyclo[1.1.1]pentylaldehyde Building Blocks

J Org Chem. 2022 Mar 4;87(5):2393-2401. doi: 10.1021/acs.joc.1c02267. Epub 2022 Jan 20.

Abstract

The bicyclo[1.1.1]pentane (BCP) motif is an emerging scaffold in medicinal chemistry because of its bioisosterism to 1,4-phenylene and 1,2-alkynyl functions. The current drawback of its use is the lack of stable versatile synthetic building blocks. Aldehydes are among the most useful functionalities in organic chemistry. In this paper, a simple one-pot procedure from aryl-halides and [1.1.1]propellane is described. Preparation of various BCP molecules is conducted to showcase the versatility of these stable intermediates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes* / chemistry
  • Chemistry, Organic*
  • Chemistry, Pharmaceutical

Substances

  • Aldehydes