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Catalytic Enantioselective Cloke–Wilson Rearrangement |
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| Authors: | Alesandere Ortega Dr Rubén Manzano Prof?Dr Uxue Uria Prof?Dr Luisa Carrillo Prof?Dr Efraim Reyes Prof?Dr Tomas Tejero Prof?Dr Pedro Merino Prof?Dr Jose L Vicario |
| Institution: | 1. Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), Bilbao, Spain;2. Instituto de Síntesis Química y Catálisis Homogénea (ISQH), Universidad de Zaragoza CSIC, Zaragoza, Spain;3. Instituto de Biocomputación y Fisica de Sistemas Complejos (BIFI), Universidad de Zaragoza, Zaragoza, Spain |
| Abstract: | Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor‐acceptor cyclopropane substrate by the chiral Brønsted acid catalyst to promote the ring‐opening event, thus generating a carbocationic intermediate that subsequently undergoes cyclization. Computational studies and control experiments support this mechanistic pathway. |
| Keywords: | asymmetric catalysis carbocations organocatalysis rearrangements strained molecules |