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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
B(C6F5)3-Catalyzed Ring-Opening Reaction of Bicyclo[1.1.0]butanes with Silyl Ketene Imines
Zhongyu Yi1, Yishan Xiong1, Lin Li1
1Institute of Drug Discovery Technology and Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang 315211, P. R. China.
Abstract:
Nucleophilic addition to strained rings is an efficient approach for the synthesis of polysubstituted cyclobutanes, which are privileged structural scaffolds in many pharmaceuticals. In this work, we have developed a simple, efficient, transition-metal-free, and scalable route for the synthesis of trisubstituted methylenecyclobutanes via ring opening of bicyclo[1.1.0]butanes with silyl ketene imines, using B(C6F5)3 as the catalyst under mild reaction conditions. In this fashion, 24 new potential bioisosteres containing trisubstituted methylene cyclobutanes were obtained in good to excellent yields (up to 99% yield). Furthermore, example reactions were performed on a gram scale, and a proposed mechanism is discussed.
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