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Metalloradical activation of ?-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes.

ABSTRACT: For the first time, ?-formyldiazoacetates have been successfully applied for the asymmetric cyclopropanation of alkenes via Co(ii)-based metalloradical catalysis. The cobalt(ii) complex of the D₂-symmetric chiral amidoporphyrin [Co(3,5-Di ^t Bu-ChenPhyrin)] is an effective metalloradical catalyst that can activate ?-formyldiazoacetates to cyclopropanate both aromatic and aliphatic olefins with varied electronic properties, affording the synthetically useful 1,1-cyclopropaneformylesters in high yields with both high diastereo- and enantioselectivity.

SUBMITTER: Xu X

PROVIDER: S-EPMC5605771 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes.

Xu Xue X Wang Yong Y Cui Xin X Wojtas Lukasz L Zhang X Peter XP

Chemical science 20170331 6

For the first time, α-formyldiazoacetates have been successfully applied for the asymmetric cyclopropanation of alkenes via Co(ii)-based metalloradical catalysis. The cobalt(ii) complex of the D2-symmetric chiral amidoporphyrin [Co(3,5-Di t Bu-ChenPhyrin)] is an effective metalloradical catalyst that can activate α-formyldiazoacetates to cyclopropanate both aromatic and aliphatic olefins with varied electronic properties, affording the synthetically use ...[more]

PMID: 28959396

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