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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Strain-Release Functionalization of N-Aryl Bicyclo[1.1.0]butane Sulfonamides to Access Spirocyclic Sultams
Manish Ranjan Sarkar1, Tushar Singha1, Subhayan Aich1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka 560012, India.
Abstract:
Sultams are recognized as important scaffolds in drug discovery and medicinal chemistry. When integrated into spirocyclic structures, especially those containing cyclobutane units, they provide conformational rigidity and a well-defined three-dimensional structure, which enhances their physicochemical and pharmacokinetic properties. Despite their potential, the synthesis of spirocyclobutyl sultams has been scantly explored. In this study, we present a general strategy for synthesizing spirocyclobutyl benzosultams by combining the strain release of N-aryl bicyclo[1.1.0]butane sulfonamides with photoredox catalysis. This method enables the construction of a diverse library of functionalized spirocyclobutyl benzosultams by incorporation of a wide range of radicals, including SCF3, SCN, SO2R, and P(O)(OR)2.
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