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Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water.

ABSTRACT: The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)2 and a chiral 2,2'-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis. Both solid and liquid substrates were suitable despite being insoluble in water.

SUBMITTER: Zhu L

PROVIDER: S-EPMC4661013 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water.

Zhu Lei L Kitanosono Taku T Xu Pengyu P Kobayashi Shū S

Beilstein journal of organic chemistry 20151027

The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)2 and a chiral 2,2'-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis. Both solid and liquid substrates were suitable despite being insoluble in water. ...[more]

PMID: 26664621

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