TRANSACETOACETYLATION WITH TERT-BUTYL ACETOACETATE - SYNTHETIC APPLICATIONS

Reaction of various nucleophiles with tert-butyl acetoacetate (t-BAA, 1a) is shown to be a convenient method for the preparation of a wide variety of acetoacetic acid derivatives. This material can be used to prepare acetoacetates and acetoacetamides from a wide variety of alcohols and amines. Reaction of 1a with an unhindered primary amine such as n-heptylamine under standard conditions gives unwanted byproducts due to the formation of the enamines 24 and 25. Formation of these byproducts can be minimized by dilution and/or altering the mode of addition.