Affiliation:
1. Organisch-Chemisches Institut Westfälische Wilhelms-Universität Münster Corrensstraße 40 48149 Münster Germany
Abstract
AbstractSynthesis of bicyclic scaffolds has attracted tremendous attention because they are playing an important role as saturated bioisosteres of benzenoids in modern drug discovery. Here, we report a BF3‐catalyzed [2π+2σ] cycloaddition of aldehydes with bicyclo[1.1.0]butanes (BCBs) to access polysubstituted 2‐oxabicyclo[2.1.1]hexanes. A new kind of BCB containing an acyl pyrazole group was invented, which not only significantly facilitates the reactions, but can also serve as a handle for diverse downstream transformations. Furthermore, aryl and vinyl epoxides can also be utilized as substrates which undergo cycloaddition with BCBs after in situ rearrangement to aldehydes. We anticipate that our results will promote access to challenging sp3‐rich bicyclic frameworks and the exploration of BCB‐based cycloaddition chemistry.
Funder
Alexander von Humboldt-Stiftung
Deutsche Forschungsgemeinschaft
Subject
General Chemistry,Catalysis
Cited by
15 articles.
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