Synthesis and Use of Versatile [1.1.1]Bicyclopentylaldehyde Building Blocks

01 September 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The [1.1.1] bicyclopentane (BCP) motif is an emerging scaffold in medicinal chemistry due to its bioisosterism to 1,4-phenylene and 1,2-alkynyl functions. Current drawback of their use is the lack of stable versatile synthetic building blocks. Aldehydes are amongst 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 in-termediates.

Keywords

synthesis
bicyclopentane
propellane
building-block
bioisosterism

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