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Strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes

Qianqian Hu, Jie Chen, Yang Yang, Hui Yang, Ling Zhou

2024Tetrahedron Chem112 citationsDOIOpen Access PDF

Abstract

Bicyclo[1.1.0]butanes (BCBs) and [1.1.1]propellanes (tricyclo[1.1.1.01,3]pentanes, TCPs) are structurally unique compounds with different chemical properties. Strain-release driven reactions have emerged as an atom- and step-economic strategy for the organic synthesis. Using this strategy, a variety of functional ring molecules have been efficiently synthesized, including various cyclobutane molecules, bicyclo[2.1.1]hexanes, bicyclo[1.1.1]pentanes, and others. More specifically, these strain release-driven reactions include aspects of nucleophilic addition, radical addition, electrophilic or transition metal catalysis. This review will discuss the recent developments in the strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes.

Topics & Concepts

Bicyclic moleculeStrain (injury)PropellaneStereochemistryChemistryMedicinal chemistryBiologyAnatomyCatalysis and Oxidation ReactionsAsymmetric Synthesis and CatalysisMolecular spectroscopy and chirality