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Paper | Regular issue | Vol 57, No. 6, 2002, pp.1091-1099
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9475
One-Step Synthesis of Optically Active Cyclic Polyamines Containing Helicene

Shinobu Honzawa, Shinya Chiba, Hitoshi Okubo, and Masahiko Yamaguchi*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan

Abstract

Chiral macrocyclic tetraamines containing four helicenes were effectively synthesized in one-step. Reductive coupling of a (P)-helicenedi(methylamine) and a (P)-helicenedicarbaldehyde gives a cyclic (P,P,P,P)-tetramer in 88% yield. The (P,M,P,M)-diastereomer was effectively synthesized from the (M)-diamine and the (P)-dialdehyde in 66% yield. The intermediate (P,P,P,P)-imine and (P,M,P,M)-imine can be isolated also in high yields. The reductive coupling of achiral arenes, m-phenylenedi(methylamine) and m-phenylenedicarbaldehyde gives the cyclic tetramer in 47% yield, which is accompanied by the higher cyclic oligomers containing hexamer (18%) and octamer (3%). The condensed benzene ring system of the helicene appears to play an important role in the high yielding cyclic tetramerization.