Abstract

Chiral cyclam (1,4,8,11-tetraazacyclotetradecane) derivatives were synthesized stepwise from chiral mono-Boc-1,2-diamines and (dialkyl)malonyl dichloride via the open diamide-di-(N-Boc-amino) intermediates (65-91%). Deprotection and ring closure with a second malonyl unit afforded the cyclam tetraamide precursors (80-95%). The new protocol allowed preparation of the target cyclam derivatives (53-59%) by a final optimized hydride reduction. Both the open tetraamine intermediates and the cyclam derivatives successfully coordinated with AuCl₃ to give moderate to excellent yields (50-96%) of the corresponding novel tetracoordinated N,N,N,N-Au(III) complexes with alternating five- and six-membered chelate rings. Testing of catalytic ability of the cyclam based N,N,N,N-Au(III) complexes demonstrated high catalytic activity of some complexes in selected test reactions (full conversion in 1-24h, 62-97% product yields).

Keywords: Au(III); Coordination studies; Cyclopropanation; carboalkoxylation ; cyclam derivatives

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Reiersølmoen, A. C.; Solvi, T. N.; Fiksdahl, A. Beilstein Arch. 2020, 2020124. doi:10.3762/bxiv.2020.124.v1

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