Synthesis of modified Weinreb amides: N-tert-butoxy-N-methylamides as effective acylating agents |
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| Authors: | Olivier Labeeuw Jean-Pierre Genêt |
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| Institution: | Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR CNRS 7573, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France |
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| Abstract: | 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%. |
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| Keywords: | N-Methyl-O-tert-butylhydroxylamide Acylation Aldehydes Ketones Weinreb amides |
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