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Issue 66, 2019
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Asymmetric synthesis of α-chiral β-hydroxy allenes: copper-catalyzed γ-selective borylative coupling of vinyl arenes and propargyl phosphates

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Abstract

Copper-catalyzed enantioselective coupling of vinyl arenes with bis(pinacolato)diboron (B2pin2) and propargylic phosphates is presented. The protocol affords a facile route to enantioenriched α-branched allenes with a versatile pinacolboronate group at the β-position with high enantioselectivity up to 98 : 2 er. In the presence of a copper catalyst complexed with a chiral bisphosphine ligand, catalytic assembly of α-chiral β-hydroxy allenes was accomplished through highly selective γ-addition of a borylalkyl copper species to propargyl substrates, followed by oxidation. Catalyst-controlled divergent cyclization reactions of the resulting allenes led to concise syntheses of enantioenriched dihydropyran and dihydrofuran rings without any loss of chiral purity.

Graphical abstract: Asymmetric synthesis of α-chiral β-hydroxy allenes: copper-catalyzed γ-selective borylative coupling of vinyl arenes and propargyl phosphates

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Article information


Submitted
30 May 2019
Accepted
23 Jul 2019
First published
24 Jul 2019

Chem. Commun., 2019,55, 9813-9816
Article type
Communication

Asymmetric synthesis of α-chiral β-hydroxy allenes: copper-catalyzed γ-selective borylative coupling of vinyl arenes and propargyl phosphates

J. T. Han and J. Yun, Chem. Commun., 2019, 55, 9813
DOI: 10.1039/C9CC04165F

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