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Silver‐Enabled Cycloaddition of Bicyclobutanes with Isocyanides for the Synthesis of Polysubstituted 3‐Azabicycloheptanes
Ist Teil von
Angewandte Chemie, 2024-05, Vol.136 (21)
Ort / Verlag
Weinheim: Wiley Subscription Services, Inc
Erscheinungsjahr
2024
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Synthesis of bicyclic scaffolds has emerged as an important research topic in modern drug development because they can serve as saturated bioisosters to enhance the physicochemical properties and metabolic profiles of drug candidates. Here we report a remarkably simple silver‐enabled strategy to access polysubstituted 3‐azabicyclo[3.1.1]heptanes in a single operation from readily accessible bicyclobutanes (BCBs) and isocyanides. The process is proposed to involve a formal (3+3)/(3+2)/retro‐(3+2) cycloaddition sequence. This novel protocol allows for rapid generation of molecular complexity from simple starting materials, and the products can be easily derivatized, further enriching the BCB cycloaddition chemistry and the growing set of valuable sp3‐rich bicyclic building blocks.Dedicated to Professor Helmut Schwarz on the occasion of his 80th birthday