Synthesis of Bicyclo[1.1.0]butanes from Iodo-Bicyclo[1.1.1]pentanes
Michael D. Mandler, James Mignone, Elizabeth A. Jurica, Maximilian D. Palkowitz, Darpandeep Aulakh, Anthony N. Cauley, Christopher A. Farley, Shasha Zhang, Sarah C. Traeger, Amy A. Sarjeant, Anthony Paiva, Heidi L. Perez, Bruce A. Ellsworth, Alicia Regueiro‐Ren
Abstract
We describe a two-step process for the synthesis of substituted bicyclo[1.1.0]butanes. A photo-Hunsdiecker reaction generates iodo-bicyclo[1.1.1]pentanes under metal-free conditions at room temperature. These intermediates react with nitrogen and sulfur nucleophiles to afford substituted bicyclo[1.1.0]butane products.
Topics & Concepts
Bicyclic moleculeButaneChemistryNucleophileOrganic chemistryMedicinal chemistryCatalysisOxidative Organic Chemistry ReactionsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms