Tetrahedron Letters p. 3073 - 3077 (2017)
Update date:2022-09-26
Topics:
Jacobsen, Eric
Chavda, Mihir K.
Zikpi, Kokou M.
Waggoner, Stephanie L.
Passini, Daniel J.
Wolfe, Jesse A.
Larson, Robert
Beckley, Chelsea
Hamaker, Christopher G.
Hitchcock, Shawn R.
A reagent combination of toluenesulfinic acid and trimethylacetyl chloride affords a putative trimethylacetic p-toluenesulfinic anhydride. This reagent has been used to prepare a series of sulfinate esters from primary and secondary alcohols. In addition, the reagent was used to convert Baylis-Hillman substrates into allylic sulfones. Attempts to use the reagent to convert amines to sulfinamides were unsuccessful. In contrast, the use of 2-pyrrolidinone afforded N-p-toluenesulfinyl pyrrolidinone in 64% yield. The use of a chiral 4-benzyl-1,3-oxazolidinone or 4-benzyl-1,3-oxazolidine-2-thione led to the isolation of S-p-tolyl p-toluenethiosulfonate.
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