Pyrrolidines and piperidines functional groups are found in biologically active molecules. Furthermore, sulfonic acids are used as non-classical isosteres for carboxylic acids in lead modifications pharmaceutical synthesis. In this presentation we report a novel sulfamination of tethered aminoalkenes. 3-sulfonopiperidines are obtained in good to very good yields through 6 endo-cyclization. The reaction relies on hypervalent iodine as an oxidant and is promoted by sulfuric acid, which also serves as source of an external nucleophile. Interestingly, better yields are achieved using meta-chloroperoxybenzoic acid (mCPBA) and iodobenzene (PhI) through generated hypervalent iodine in situ.

Sulfamination of tethered aminoalkenes using in situ generated hypervalent iodine

254th National Meeting (2017)

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