Anhydrides as α,β-unsaturated acyl ammonium precursors : isothiourea-promoted catalytic asymmetric annulation processes
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The asymmetric annulation of a range of alpha,beta-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, beta-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).
Robinson , E R T , Fallan , C , Simal , C , Slawin , A M Z & Smith , A D 2013 , ' Anhydrides as α,β-unsaturated acyl ammonium precursors : isothiourea-promoted catalytic asymmetric annulation processes ' Chemical Science , vol. 4 , pp. 2193-2200 . DOI: 10.1039/c3sc50199j
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