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

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2024 Jan 22

PMID 38251922

Authors

Rebecca I Revie

Benjamin J Whitaker

Bhaskar Paul

Russell C Smith

Edward A Anderson

Affiliations

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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 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 substituted arenes and pyridines.

Citing Articles

Synthesis of bicyclo[3.1.1]heptanes, meta-substituted arene isosteres, from [3.1.1]propellane.

Paul B, Dasgupta A, Frank N, Nugent J, Anderson E Nat Protoc. 2025; .

PMID: 39962198 DOI: 10.1038/s41596-024-01109-5.

Three-dimensional saturated C(sp)-rich bioisosteres for benzene.

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