Stereogenic: Cis -2-substituted- N -acetyl-3-hydroxy-indolines via ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation
Ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation of racemic 2-substituted-N-acetyl-3-oxoindolines to cis-2-substituted-N-acetyl-3-hydroxyindolines is reported. Using the homochiral {Ru[TfDPEN](p-cymene)} catalyst with S/C = 400 in a HCO2H/Et3N mixture, up to >99.9% ee and >99:1 dr are obtained with high yields (79-98%). This method provides the first example of preparing enantiomerically pure indolines through asymmetric transfer hydrogenation (ATH).
Synthesis of Novel 1-Phenyl-1H-indole-2-carboxylic Acids. I. Utilization of Ullmann and Dieckmann Reactions for the Preparation of 3-Hydroxy, 3-Alkoxy, and 3-Alkyl Derivatives
Methods for the synthesis of novel 3-hydroxy, 3-alkoxy, and 3-alkyl indole-2-carboxylic acids and esters are described.Dieckmann cyclization of various 2-benzoic acid diesters yielded 1-unsubstituted-, 1-methyl-, and 1-phenyl-3-hydro
Unangst, Paul C.,Connor, David T.,Stabler, S. Russell,Weikert, Robert J.
p. 811 - 815
(2007/10/02)
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