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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Base-Mediated Tandem Michael Addition and SuFEx Cyclization for the Synthesis of Sultone-Containing Spirooxindoles
Kimberleigh B Govender1, Sandile B Simelane1, Lloyd C Chetty1
1Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4001, South Africa.
None:
Sulfur-containing spirooxindoles are recognized for their significant biological activity, yet accessing these compounds with diverse heteroatoms in the spirocyclic core has remained challenging. This study introduces a simple and efficient base-mediated tandem Michael addition reaction and SuFEx cyclization to synthesize novel sultone-containing spirooxindoles. The transformation occurred in a green solvent, which proved essential in suppressing side reactions, leading to the successful synthesis of 20 novel sultone-spirooxindoles and two sulfonates that are resistant to cyclization. Additionally, a chiral variant of the reaction was explored, laying the groundwork for the future development of enantioselective methods.
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