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

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...

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Published inChemical science (Cambridge) Vol. 4; no. 5; pp. 2193 - 2200
Main Authors Robinson, Emily R. T., Fallan, Charlene, Simal, Carmen, Slawin, Alexandra M. Z., Smith, Andrew D.
Format Journal Article
LanguageEnglish
Published 01.04.2013
Subjects
Anhydrides
Asymmetry
Catalysis
Catalysts
Esters
Ketones
Precursors
Ring opening
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ISSN2041-6520
2041-6539
DOI10.1039/c3sc50199j

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Summary: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).
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ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc50199j