Nucleophile Aminoalkylierung mit Thiopivalamiden

Nucleophilic Aminoalkylation with Thiopivalamides Vorläufige Mitt. [1]. Of the twelve thioamides 7a‐e and 8a‐g , only N,N ‐dimethylthiopivalamide ( 7a ) could be metallated at the CH‐group in a ‐position to the N‐Atom. The reagent 9 thus obtained (Table 1) reacts in high yields with primary haloalkanes, with aldehydes, and with non‐enolizable ketones (Table 2) . As shown in Scheme 1 , the products can be hydrolyzed to pivalamides, cleaved to secondary amines, or reduced to neopentylamines (see 18/19, 15 /equation (4) and (5), and 16/20 , respectively).