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Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

ABSTRACT: We report non-decarbonylative Mizoroki-Heck reactions of amide derivatives. The transformation relies on the use of nickel catalysis and proceeds using sterically hindered tri- and tetrasubstituted olefins to give products containing quaternary centers. The resulting polycyclic or spirocyclic products can be obtained in good yields. Moreover, a diastereoselective variant of this method gives access to an adduct bearing vicinal, highly substituted sp3 stereocenters. These results demonstrate that amide derivatives can be used as building blocks for the assembly of complex scaffolds.

SUBMITTER: Medina JM

PROVIDER: S-EPMC5669036 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

Medina Jose M JM Moreno Jesus J Racine Sophie S Du Shuaijing S Garg Neil K NK

Angewandte Chemie (International ed. in English) 20170503 23

We report non-decarbonylative Mizoroki-Heck reactions of amide derivatives. The transformation relies on the use of nickel catalysis and proceeds using sterically hindered tri- and tetrasubstituted olefins to give products containing quaternary centers. The resulting polycyclic or spirocyclic products can be obtained in good yields. Moreover, a diastereoselective variant of this method gives access to an adduct bearing vicinal, highly substituted sp<sup>3</sup> stereocenters. These results demon ...[more]

PMID: 28467029

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Enantioselective nickel-catalyzed Mizoroki–Heck cyclizations of amide electrophiles† † Electronic supplementary information (ESI) available. CCDC 2271421. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc05797f

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