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Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides.

ABSTRACT: Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out.

SUBMITTER: Miyaji R 

PROVIDER: S-EPMC5550815 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides.

Miyaji Ryota R   Wada Yuuki Y   Matsumoto Akira A   Asano Keisuke K   Matsubara Seijiro S  

Beilstein journal of organic chemistry 20170802

Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out. ...[more]

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