Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2015-01-07

Journal: TETRAHEDRON

Included Journals: Scopus、SCIE

Volume: 71

Issue: 1

Page Number: 85-90

ISSN: 0040-4020

Key Words: Methylhydrazine; beta-Keto esters; Cinchona-alkaloid; Molecular oxygen; Organocatalysis

Abstract: Methylhydrazine-induced alpha-hydroxylation of beta-dicarbonyl compounds was achieved using O-2 as the oxygen source. This reaction provides an efficient approach to enantioenriched alpha-hydroxy beta-dicarbonyl compounds, which are valuable substances and widely used in the chemical and pharmaceutical industry. A wide variety of beta-keto esters could undergo this oxidation to give the corresponding products in excellent yields (up to 95%) and with good enantioselectivities (up to 85% ee). The mild reaction conditions and the use of molecular oxygen as oxidant make this protocol very environmentally friendly and practical. (C) 2014 Elsevier Ltd. All rights reserved.