# Synthesis of Heterocycle-Substituted Bicyclo[3.1.1]heptanes and Aza-bicyclo[3.1.1]heptanes via Photocatalytic Minisci Reaction

**Authors:** Rebecca
I. Revie, Benjamin J. Whitaker, Bhaskar Paul, Russell C. Smith, Edward A. Anderson

PMC · DOI: 10.1021/acs.orglett.3c03684 · 2024-01-22

## 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.

## Key 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.

## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11020156/full.md

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Source: https://tomesphere.com/paper/PMC11020156