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Issue 5, 2015
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Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

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Abstract

The single-step construction of various densely oxygenated carboskeletons was achieved by radical-based two- and three-component coupling reactions of sugar derivatives, without the need for light or heat. Et3B/O2-mediated decarbonylation readily converted α-alkoxyacyl tellurides to α-alkoxy carbon radicals, which intermolecularly added to glyoxylic oxime ether or enones to provide the two-component adducts. Furthermore, the three-component adducts were produced by an intermolecular aldol reaction between the aldehyde and the boron enolates generated by capture of the two-component radical intermediates by Et3B. This powerful coupling method serves as a novel strategy for the convergent synthesis of polyol natural products.

Graphical abstract: Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

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Publication details

The article was received on 06 Feb 2015, accepted on 05 Mar 2015 and first published on 06 Mar 2015


Article type: Edge Article
DOI: 10.1039/C5SC00457H
Citation: Chem. Sci., 2015,6, 2765-2769
  • Open access: Creative Commons BY-NC license
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    Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

    M. Nagatomo, D. Kamimura, Y. Matsui, K. Masuda and M. Inoue, Chem. Sci., 2015, 6, 2765
    DOI: 10.1039/C5SC00457H

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