Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons† †Electronic supplementary information (ESI) available: Experimental protocols, characterization data, and NMR spectra of all new compounds. See DOI: 10.1039/c5sc00457h

نویسندگان

  • Masanori Nagatomo
  • Daigo Kamimura
  • Yuki Matsui
  • Keisuke Masuda
  • Masayuki Inoue
چکیده

The single-step construction of various densely oxygenated carboskeletons was achieved by radical-based twoand three-component coupling reactions of sugar derivatives, without the need for light or heat. Et3B/ O2-mediated decarbonylation readily converted a-alkoxyacyl tellurides to a-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.

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Dual gold and photoredox catalysed C–H activation of arenes for aryl–aryl cross couplings† †Electronic supplementary information (ESI) available: Experimental procedures, full optimisation tables, control reaction, mechanistic studies, characterisation data and copies of NMR spectra of new compounds. See DOI: 10.1039/c6sc05469b Click here for additional data file.

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عنوان ژورنال:

دوره 6  شماره 

صفحات  -

تاریخ انتشار 2015