Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and β-keto esters using DBFOX ligand

…, N Shibata, J Nagai, S Nakamura, T Toru…

Index: Ishimaru, Takehisa; Shibata, Norio; Nagai, Jun; Nakamura, Shuichi; Toru, Takeshi; Kanemasa, Shuji Journal of the American Chemical Society, 2006 , vol. 128, # 51 p. 16488 - 16489

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Citation Number: 198

Abstract

The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2- oxindoles using the DBFOX-Zn (II) complex, leading to pharmaceutically important chiral 3- hydroxy-2-oxindoles was described. The structure of oxidant was found to play an important role to increase the enantioselectivity. The methodology has successfully applied to the highly enantioselective hydroxylation of β-keto esters using the DBFOX-Ni (II) complex.