Synthesis of chiral polyazamacrocycles of variable ring size

Organic & Biomolecular Chemistry
Seiji KamiokaTakayuki Doi


Synthesis and structure elucidation of optically active tri-, tetra-, and penta-azamacrocycles having 4-methoxyphenyl pendants are described. Regioselective ring opening of a nosylaziridine with secondary benzyl amines was repeatedly performed to afford the cyclization precursors. Intramolecular N-alkylation of N-(omega-haloalkyl) nosylamide provided tri-, tetra-, and penta-azamacrocycles. On the basis of our study of the tetra-azamacrocycle previously elucidated by X-ray single-crystal analysis and in solution by NMR analysis, we conclude that the tri-azamacrocycle does not mainly have a vase-type conformation because of the steric hindrance of the 4-methoxyphenyl groups but the penta-azamacrocycle has a vase-type conformation in CDCl(3) and in CD(2)Cl(2). The vase-type conformation of the penta-azamacrocycle is, however, not as much stable as that observed in the tetra-azamacrocycle because conformational flexibility of the penta-azamacrocycle was observed in deuterated benzene.


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Dec 5, 2003·Journal of the American Chemical Society·Todd M CorneillieC F Meares
Feb 7, 2004·Chemical Communications : Chem Comm·Toshiyuki Kan, Tohru Fukuyama
Sep 8, 2004·Organic & Biomolecular Chemistry·J Erik W ScheuermannMichael Watkinson
Nov 29, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Mark WoodsA Dean Sherry
Jul 8, 2008·Chemistry : a European Journal·M Meser AliA Dean Sherry
May 13, 2009·Organic Letters·Seiji KamiokaTakayuki Doi
May 23, 2009·Chemical Communications : Chem Comm·Hyun-Soon ChongSantosh B Mhaske
Jun 6, 2009·Journal of the American Chemical Society·Emily L QueChristopher J Chang
Jun 26, 2009·Organic Letters·Kazuya KikuchiTetsuo Nagano
May 3, 2002·Angewandte Chemie·Fraser HofJulius Rebek

Related Concepts

Aza Compounds
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