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

Takehisa Ishimaru; Norio Shibata; Jun Nagai; Shuichi Nakamura; Takeshi Toru; Shuji Kanemasa

doi:10.1021/ja0668825

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

J Am Chem Soc. 2006 Dec 27;128(51):16488-9. doi: 10.1021/ja0668825.

Authors

Takehisa Ishimaru¹, Norio Shibata, Jun Nagai, Shuichi Nakamura, Takeshi Toru, Shuji Kanemasa

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

PMID: 17177383
DOI: 10.1021/ja0668825

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 beta-keto esters using the DBFOX-Ni(II) complex.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Esters / chemical synthesis*
Esters / chemistry
Heterocyclic Compounds, 3-Ring / chemistry
Hydroxylation
Indoles / chemical synthesis*
Indoles / chemistry
Ketones / chemical synthesis*
Ketones / chemistry
Ligands
Molecular Structure
Nickel / chemistry
Oxazoles / chemistry
Oxindoles
Stereoisomerism
Zinc / chemistry*

Substances

Esters
Heterocyclic Compounds, 3-Ring
Indoles
Ketones
Ligands
Oxazoles
Oxindoles
2-oxindole
Nickel
Zinc