Preparation of an isocyanide having a removable N-substituent and its application to the stereoselective synthesis of 2-amino alcohols are described. 4-(tert-Butyldimethylsiloxy)-2, 6- xylyl isocyanide was prepared from commercially available 3, 5-xylenol. The isocyanide underwent a samarium iodidemediated coupling reaction with organic halides and carbonyl compounds. Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-( ...
