2009
DOI: 10.1055/s-0029-1217567
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Trapping of an Ammonium Ylide with Activated Ketones: Synthesis of β-Hydroxy-α-Amino Esters with Adjacent Quaternary Stereocenters

Abstract: A novel Rh 2 (OAc) 4 -catalyzed three-component reaction of diazoacetates, anilines, and activated ketones via ammonium ylide trapping processes is reported. The reaction of isatins afforded a-amino-b-hydroxy esters bearing the 3-substituted 3-hydroxyindolin-2-one moiety with vicinal quaternary carbon centers in one step with high chemo-and diastereoselectivity. Extension of the reaction to acyclic a-keto esters afforded 2-hydroxy-2-alkyl-3-aryl-3-(phenylamino) succinates in moderate yield and diastereoselecti… Show more

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