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The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues.

ABSTRACT: The analogous imino-variant of the Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylated pyrimidine derivatives as nucleophilic trapping partners culminated in an expedient synthetic route to carbocyclic nucleoside analogues. The potential application of silylated nucleobases to intercept the oxyallyl cation in other variants of the Nazarov reaction provides vast opportunities to develop new strategies for the formation of carbocyclic nucleoside analogues.

SUBMITTER: William R

PROVIDER: S-EPMC5954973 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues.

William Ronny R Leng Wei Lin WL Wang Siming S Liu Xue-Wei XW

Chemical science 20151027 2

The analogous imino-variant of the Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylated pyrimidine derivatives as nucleophilic trapping partners culminated in an expedient synthetic route to carbocyclic nucleoside analogues. The potential application of silylated nucleobases to interce ...[more]

PMID: 29896374

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