Stereoisomerism in macrocyclic bis(piperidones)

A. M. Belostotskii; A. B. Shapiro

doi:10.1007/bf00478137

Stereoisomerism in macrocyclic bis(piperidones)

A. M. Belostotskii
, A. B. Shapiro

RAS - N.N. Semenov Institute of Chemical Physics

Research output: Contribution to journal › Article › peer-review

Abstract

The reaction of a polysubstituted 3,5-dimethylene-4-piperidone with aliphatic diamines leads to macrocyclic products, namely, 3,3′,5,5′-di(methylaminoalkyl-aminomethyl)-bridged bis(piperidones). The latter compounds are formed as mixtures of cis, trans-isomers, and isolated in the form of cis,cis-isomers. ¹³C-NMR spectral analysis has shown that these compounds also exhibit characteristic syn-anti isomerism associated with the relative orientation of the 3,5-substituents on opposite piperidone rings.

Original language	English
Pages (from-to)	1011-1016
Number of pages	6
Journal	Chemistry of Heterocyclic Compounds
Volume	22
Issue number	9
DOIs	https://doi.org/10.1007/bf00478137
State	Published - Sep 1986
Externally published	Yes

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AB - The reaction of a polysubstituted 3,5-dimethylene-4-piperidone with aliphatic diamines leads to macrocyclic products, namely, 3,3′,5,5′-di(methylaminoalkyl-aminomethyl)-bridged bis(piperidones). The latter compounds are formed as mixtures of cis, trans-isomers, and isolated in the form of cis,cis-isomers. 13C-NMR spectral analysis has shown that these compounds also exhibit characteristic syn-anti isomerism associated with the relative orientation of the 3,5-substituents on opposite piperidone rings.

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Stereoisomerism in macrocyclic bis(piperidones)

Abstract

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