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Synthesis of chiral azamacrocycles using the bis(α-chloroacetamide)s derived from chiral 1,2-diphenylethylenediamine

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

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
650 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Optically active diphenyl‐substituted tetraaza‐12‐crown‐4 diamide (10), tetraaza‐15‐crown‐5 diamide (12), tetraaza‐18‐crown‐6 diamide (11), and hexaaza‐18‐crown‐6 diamide (9) ligands were prepared by treating the appropriate secondary diamines with the (R,R)‐ and (S,S)‐ forms of 1,2‐bis(N‐methyl‐α‐chloracetamido)‐1,2‐diphenylethane (20). Macrocyclic diamides 9 and 10 were reduced to form the optically active diphenyl‐substituted hexaaza‐18‐crown‐6 (13) and tetraaza‐12‐crown‐4 (14), respectively. Reduction of macrocyclic diamide ligands 11 and 12 gave a complex mixture of products from which the desired tetraaza‐15‐crown‐5 and 18‐crown‐6 compounds could not be isolated. Dichloride 20 was prepared by treating the chiral forms of 1,2‐ diphenylethylenediamine with chloroacetic anhydride or chloroacetyl chloride. The crystal structures for the (R,R)‐form of dichloride 20 and the (S,S)‐forms of macrocycles 10 and 11 are reported.

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