Journal of the Chemical Society, Dalton Transactions p. 1127 - 1132 (1987)
Update date:2022-08-11
Topics:
Miyamura, Kazuo
Hata, Kazuhiko
Makino, Tadashi
Saburi, Masahiko
Yoshikawa, Sadao
The reaction of bis<(3S)-3-aminopiperidine>copper(II) with but-3-en-2-one in methanol in the presence of ammonia gives an optically active tetra-azamacrocyclic comlex in ca. 80percent yield.Analogous optically active complexes are also obtained from bis<(3S)-3-aminohexahydroazepine>copper(II) or bis<(2S)-2-(aminomethyl)pyrrolidine>copper(II) by the same procedure.The introduction of methyl and/or a hydroxyl group at the C4 position of but-3-en-2-one leads to a decrease in the reactivity of the ketones, and changes the species and distribution of the reaction products.In particular, when the C4 position is fully substituted with methyl groups, C-N bond formation with the secondary amino group no longer proceeds.The change in the reaction mode due to the substituents at C4 is discussed.
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