DOI: 10.1021/acs.orglett.6c03497 ISSN: 1523-7060
Polar and e-Radical Strain-Release Strategies for Accessing Functionalized 2-Oxabicyclo[2.1.1]hexan-3-ones from Bicyclo[1.1.0]butanes
Samuele Usai, Giulia Monda, Elena Graziano, Andrea Brunetti, Leonardo Degennaro, Luisa Pisano, Marco Bandini, Marco Colella, Giulio Bertuzzi, Renzo LuisiAbstract
2-Oxabicyclo[2.1.1]hexanes (OBHs) have emerged as valuable saturated aromatic replacements, whereas their lactone analogues, 2-oxabicyclo[2.1.1]hexan-3-ones (OBHOs) remain underexplored, because of limited synthetic access. Herein, we report complementary polar and electrochemical strain-release strategies for the modular synthesis of 1,4-difunctionalized OBHOs from bicyclo[1.1.0]butane carboxylic acids. The two activation modes provide complementary perspectives toward the chemical space expansion of this underexplored scaffold.