ELECTROPHILIC AMINATION OF 2-AZADIENES

2-Azadienes 1 bearing a trialkylsilyloxy group on position 3 can be re garded as carboxylic acid synthons. Their cycloadditions with several classes of nitroso compounds have been studied in details as well as t he transformation of the adducts into alpha-amino acids. This study sh owed that arylnitroso compounds such as nitrosobenzene reacted with 2- azadienes to give adducts that are potential precursors of alpha-N-ary lamino acids. We have outlined an important limitation to the use of a lpha-chloronitroso compounds. They are not compatible with highly func tionalized dienes like 2-azadienes. On the other hand alpha-cyanonitro so and acylnitroso compounds reacted with azadienes to give adducts wh ich were readily converted into alpha-amino acid derivatives. Copyrigh t (C) 1996 Elsevier Science Ltd