Highly diastereoselective nucleophilic addition reactions of masked acyl cyanide reagents to tert-butanesulfiminides

Addition reactions of dicyanomethyl tert-butyldimethylsilyl ether (H–MAC–TBS) to optically active tert-butanesulfinimides afforded α-amino acid precursors in excellent yields and with high diastereoselectivities.

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(RS)-2-Methyl-N-(4-tifluoromethylbenzylidene)propane-2-sulfinamideC9H6F3NOSEe = 70%[α]D22=-78.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (RS)