Asymmetric Radical Addition of Ethers to Enantiopure N-p-Toluenesulfinyl Aldimines, Mediated by Dimethylzinc−Air
Organic Letters2006Vol. 8(25), pp. 5729–5732
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Abstract
Asymmetric radical addition of ethers to enantiopure aromatic N-p-toluenesulfinyl aldimines has been achieved. The requisite radicals were generated by dimethylzinc-air. Lewis acid activation of the N-p-toluenesulfinyl aldimines followed by radical addition gives a mixture of sulfinamide and sulfonamide products. Subsequent treatment of the mixture with dry m-CPBA affords the sulfonamide product in enantiomerically enriched form. [reaction: see text]
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