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Issue 4, 2017
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Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

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Abstract

An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.

Graphical abstract: Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

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Publication details

The article was received on 10 Oct 2016, accepted on 28 Jan 2017 and first published on 30 Jan 2017


Article type: Edge Article
DOI: 10.1039/C6SC04522G
Citation: Chem. Sci., 2017,8, 3026-3030
  • Open access: Creative Commons BY license
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    Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

    G. Hazra, S. Maity, S. Bhowmick and P. Ghorai, Chem. Sci., 2017, 8, 3026
    DOI: 10.1039/C6SC04522G

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