hydroxy ketones prepared by regioselective hydroacylationElectronic supplementary information (ESI) available: Experimental procedures, characterization data for new compounds. See DOI: 10.1039/c1sc00634g

We report an intermolecular hydroacylation of allylic alcohols with salicylaldehydes to afford -hydroxy aryl ketones in 7394% yields as single regioisomers. The reactivity and regioselectivity were promoted by catalytic amounts of a phosphinite that forms a dynamic covalent bond with the allylic alc...

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Main Authors Murphy, Stephen K, Coulter, Matthew M, Dong, Vy M
Format Journal Article
LanguageEnglish
Published 10.01.2012
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Abstract We report an intermolecular hydroacylation of allylic alcohols with salicylaldehydes to afford -hydroxy aryl ketones in 7394% yields as single regioisomers. The reactivity and regioselectivity were promoted by catalytic amounts of a phosphinite that forms a dynamic covalent bond with the allylic alcohol. Hydroacylation of 1,2- and 1,1-disubstituted olefins generates -hydroxy aryl ketones bearing tertiary and quaternary centers, respectively. By applying cooperative catalysis, we achieve a regioselective hydroacylation of allylic alcohols to afford formal aldol products.
AbstractList We report an intermolecular hydroacylation of allylic alcohols with salicylaldehydes to afford -hydroxy aryl ketones in 7394% yields as single regioisomers. The reactivity and regioselectivity were promoted by catalytic amounts of a phosphinite that forms a dynamic covalent bond with the allylic alcohol. Hydroacylation of 1,2- and 1,1-disubstituted olefins generates -hydroxy aryl ketones bearing tertiary and quaternary centers, respectively. By applying cooperative catalysis, we achieve a regioselective hydroacylation of allylic alcohols to afford formal aldol products.
Author Murphy, Stephen K
Dong, Vy M
Coulter, Matthew M
AuthorAffiliation Department of Chemistry
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  givenname: Vy M
  surname: Dong
  fullname: Dong, Vy M
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Electronic supplementary information (ESI) available: Experimental procedures, characterization data for new compounds. See DOI
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Snippet We report an intermolecular hydroacylation of allylic alcohols with salicylaldehydes to afford -hydroxy aryl ketones in 7394% yields as single regioisomers....
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