Electrophilic amination of 2-azadienes

Gouverneur, Veronique;Ghosez, Léon
(1996) Tetrahedron — Vol. 52, n° 21, p. 7585-7598 (1996)

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Abstract
2-Azadienes 1 bearing a trialkylsilyloxy group on position 3 can be regarded as carboxylic acid synthons. Their cycloadditions with several classes of nitroso compounds have been studied in details as well as the transformation of the adducts into alpha-amino acids. This study showed that arylnitroso compounds such as nitrosobenzene reacted with 2-azadienes to give adducts that are potential precursors of alpha-N-arylamino acids. We have outlined an important limitation to the use of alpha-chloronitroso compounds. They are not compatible with highly functionalized dienes like 2-azadienes. On the other hand alpha-cyanonitroso and acylnitroso compounds reacted with azadienes to give adducts which were readily converted into alpha-amino acid derivatives. Copyright (C) 1996 Elsevier Science Ltd
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Gouverneur, V., & Ghosez, L. (1996). Electrophilic amination of 2-azadienes. Tetrahedron, 52(21), 7585-7598. https://doi.org/10.1016/0040-4020(96)00268-2 (Original work published 1996)