A General Procedure for the Synthesis of Unsymmetrically Substituted Tris(β-oximinoalkyl)amines

Abstract

A first general approach to the synthesis of unsymmetrically substituted tris(β-oximinoalkyl)amines containing two or three different β-oximinoalkyl fragments has been developed. This procedure employs available aliphatic nitro compounds as starting building blocks and their silylation as the key step. This approach provides an efficient strategy for the diversity-oriented synthesis of 1,4,6,10-tetraazaadamantane derivatives.

Key words

amines - ligands - alkylation - cyclization - protecting groups

References

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4

The only known ‘unsymmetrical’ tris-oxime 1d was described in our recent communication;^² however, the method suggested for its preparation is neither general nor efficient.

13

Figure  [³] summarizes the NMR data of products 1a-l as well as the NMR data of the ‘symmetrical’ tris-oximes described in refs. 2 and 6a.