Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

Kiss, Loránd and Ouchakour, Lamiaa and Nonn, Melinda and Remete, Attila Márió (2022) Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles. SYNLETT (33). pp. 307-328. ISSN 0936-5214

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Abstract

The current Account gives an insight into the synthesis of some N-heterocyclic -amino acid derivatives and various functionalized saturated azaheterocycles accessed from substituted cycloalkenes via ring C=C bond oxidative cleavage followed by ring closing across double reductive amination. The ring-cleavage protocol has been accomplished according to two common approaches: a) Os-catalyzed dihydroxylation/ NaIO4 vicinal diol oxidation and b) ozonolysis. A comparative study on these methodologies has been investigated. Due to the everincreasing relevance of organofluorine chemistry in drug research as well as of the high biological potential of -amino acid derivatives several illustrative examples to the access of various fluorine-containing piperidine or azepane -amino acid derivatives are also presented in the current Account.

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