Synthesis of modified Weinreb amides: N-tert-butoxy-N-methylamides as effective acylating agents

Article abstract of DOI:10.1016/j.tetlet.2004.07.106

An efficient preparation of N-methyl-O-tert-butylhydroxylamine hydrochloride has been settled, which allowed the synthesis of modified Weinreb amides. Nucleophilic addition of organolithium and Grignard reagents on these N-tert-butoxy-N-methylamides afforded efficiently the corresponding ketones and reduction with DIBAL furnished the corresponding aldehydes in good yields up to 97%.