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Paper | Regular issue | Vol 41, No. 12, 1995, pp.2745-2760
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7211
Synthesis of 17- and 21-Membered Macrocycles Incorporating the Chiral 1,1'-Binaphthyl Backbone and Nitrogen, Oxygen, and Phosphorus Donor Atoms

Petra Wimmer, Gerd Klintschar, and Michael Widhalm*

*Institut für Organische Chemie, Universität Wien, 1090 Wien, Austria

Abstract

A 17-membered diaza-diphospha- and a 21-membered diaza-dioxadiphospha-macrocycle (6) and (12), respectively, including the inherent chiral binaphthyl moiety were synthesized. Titanium(IV) mediated cyclization of 1,1’-binaphthyl-2,2’-dicarbaldehyde (4) with 1,3-bis[(2-aminophenyl)phenylphosphino]propane (8) and subsequent reduction afforded 6a-c as a mixture of three diastereomers in 14% overall yield. Ligand (12) was obtained from the nickel amido complex of 8 and 2,2’-bis[2-(4-toluene)sulfonyloxyethoxy]-1,1’-binaphthyl (10a) by a template synthesis in the presence of Cs2CO3 in 63% yield. X-Ray structure determinations of cationic Ni(II) complexes of 6a and 12 were performed.