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Issue 5, 2013
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Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

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Abstract

The asymmetric annulation of a range of α,β-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, β-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).

Graphical abstract: Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

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Publication details

The article was received on 22 Jan 2013, accepted on 01 Mar 2013 and first published on 01 Mar 2013


Article type: Edge Article
DOI: 10.1039/C3SC50199J
Citation: Chem. Sci., 2013,4, 2193-2200
  • Open access: Creative Commons BY license
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    Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

    E. R. T. Robinson, C. Fallan, C. Simal, A. M. Z. Slawin and A. D. Smith, Chem. Sci., 2013, 4, 2193
    DOI: 10.1039/C3SC50199J

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