4.7 Article

Synthesis and Use of Bicyclo[1.1.1]pentylaldehyde Building Blocks

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 2393-2401

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02267

Keywords

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Funding

  1. Hungarian National Research, Development, and Innovation Office [OTKA-FK-134947, UNKP-20-365, UNKP-21-5-ELTE-1079, TKP 2020-IKA05]
  2. Servier
  3. Hungarian Academy of Sciences [BO/536/20]

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This paper presents a one-pot procedure for the synthesis of various BCP molecules, showcasing the versatility of these stable intermediates.
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.

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