Synthesis of Heterocycle-Substituted Bicyclo[3.1.1]heptanes and Aza-bicyclo[3.1.1]heptanes via Photocatalytic Minisci Reaction
Rebecca I. Revie, Benjamin J. Whitaker, Bhaskar Paul, Russell C. Smith, Edward A. Anderson
TL;DR
This paper presents a new method to create complex chemical structures using a photocatalytic reaction, which could be useful in drug development.
Contribution
A new photocatalytic method for synthesizing heterocycle-functionalized bicyclo compounds.
Findings
A mild photocatalytic Minisci-like reaction was developed for heterocycle substitution.
The method allows functionalization at the bridgehead position of BCHeps and aza-BCHeps.
The resulting compounds are relevant as bioisosteres in medicinal chemistry.
Abstract
A route toward heterocycle-functionalized bicyclo[3.1.1]heptanes (BCHeps) and aza-bicyclo[3.1.1]heptanes (aza-BCHeps) has been developed, using mild, photocatalytic Minisci-like conditions to introduce various heterocycles at the bridgehead position from readily available N-hydroxyphthalimide esters of the corresponding carboxylic acids. This chemistry enables access to heterocycle-functionalized BCHep-containing structures that are highly relevant in medicinal chemistry research as potential bioisosteres of meta-substituted arenes and pyridines.
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Taxonomy
TopicsRadical Photochemical Reactions · Synthesis and Catalytic Reactions · Cyclopropane Reaction Mechanisms