Strain-Release [2π + 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer.

Autor: Guo R; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States., Chang YC; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States., Herter L; SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 22, 4058 Basel, Switzerland.; Bio-Functional Chemistry (UMR 7199), LabEx Medalis, University of Strasbourg, 74 Route du Rhin, 67400 Illkirch-Graffenstaden, France., Salome C; SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 22, 4058 Basel, Switzerland., Braley SE; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States., Fessard TC; SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 22, 4058 Basel, Switzerland., Brown MK; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2022 May 11; Vol. 144 (18), pp. 7988-7994. Date of Electronic Publication: 2022 Apr 27.
DOI: 10.1021/jacs.2c02976
Abstrakt: Saturated bicycles are becoming ever more important in the design and development of new pharmaceuticals. Here a new strategy for the synthesis of bicyclo[2.1.1]hexanes is described. These bicycles are significant because they have defined exit vectors, yet many substitution patterns are underexplored as building blocks. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.
Databáze: MEDLINE