Sulfinamides, sigmatropic rearrangements

The [2,3] sigmatropic rearrangement of sulfenate esters 3, prepared in situ on treatment of 4-morpholinesulfenyl chloride with allylic alcohols, allows easy synthesis of diastereomeric allylic sulfinamides 4 (configurations were not established)104. 

Scheme 35 [2,3]Sigmatropic rearrangement of propargylic amidosulfenates to allenyl sulfinamides...

Unsaturated sulfinamides can also be obtained by a 2,3-sigmatropic rearrangement, again very easily affording the product with ( )-double bond geometry in most cases (Scheme 25). ... 

The use of triethyloxonium tetrafluoroborate accelerates the [3,3]-sigmatropic rearrangement of sulfinamide 6 to indole 7, as summarized in Scheme 2. 

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