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ChemInform Abstract: Synthesis of Chiral Azamacrocycles Using the Bis(α-chloroacetamide)s Derived from Chiral 1,2-Diphenylethylenediamine.

✍ Scribed by Kejiang Hu; Krzysztof E. Krakowiak; Jerald S. Bradshaw; N. Kent Dalley; Guoping Xue; Reed M. Izatt


Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Synthesis

of Chiral Azamacrocycles Using the Bis(αchloroacetamide)s Derived from Chiral 1,2-Diphenylethylenediamine.

-Polyazamacrocycles such as (VIII) and (X) are prepared by reaction of the bis(α-chloroacetamide) (VI) with a number of polyamines. The optically pure starting compounds, e.g. (I), are prepared and resolved to its (R,R)-and (S,S)forms according to the Pikul and Corey procedure. The macrocyclic diamides are reduced to form optically active compounds like tetraaza-12-crown-4 (VIII). However, reduction of macrocycles (X) gives a complex mixture of products. The solid state structures of the precursor of (VIII) and (Xb) are determined by X-ray diffraction. -(HU, KEJIANG; KRAKOWIAK, KRZYSZTOF E.;


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