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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Base-Mediated (3 + 3) Annulation of Bicyclo[1.1.0]butanes with Diarylmethyl Isothiocyanates for Access to
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Abstract:
A transition-metal-free, base-mediated (3 + 3) annulation of bicyclo[1.1.0]butanes with diarylmethyl isothiocyanates has been reported for the synthesis of 3-azabicyclo[3.1.1]heptanes. The transformation operates under mild conditions and proceeds via strain-enabled activation of the central C-C bond of the BCB framework and displays broad substrate compatibility and high yields of products. Base-mediated generation of nucleophiles and subsequent interception with the BCB framework in a (3 + 3) pathway resulted in the product formation. Scalability and post-synthetic diversification demonstrate the synthetic value of this methodology for accessing medicinally relevant azabicyclic scaffolds.
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