27955-96-0Relevant academic research and scientific papers
Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model
Zhang, Wei,Basak, Arindrajit,Kosugi, Yuji,Hoshino, Yujiro,Yamamoto, Hisashi
, p. 4389 - 4391 (2005)
(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.
Facile one-pot palladium-catalyzed sequential coupling to diarylmethanes by using aryl methyl ketones as the methylene donors
Wang, Xing,Liu, Lian-Hua,Shi, Jin-Hua,Peng, Ji,Tu, Hai-Yang,Zhang, Ai-Dong
, p. 6870 - 6877 (2013/11/06)
A novel palladium-catalyzed coupling reaction of an aryl methyl ketone with two molecules of an aryl halide to yield symmetric diarylmethanes is described. In the facile one-pot reaction, the aryl methyl ketone acts as a formal methylene donor. The experimental facts, including TLC monitoring, speculated intermediates as the raw materials, analysis of the cesium benzoate coproduct by ex situ IR spectroscopy, and the cross-coupling reactions of two different aryl halides, indicate a mechanism involving a palladium-catalyzed sequential two-step coupling process, in which the presence of a trace amount of H 2O is indispensable. The reaction is applicable to a broad spectrum of substrates and delivers the products in good to excellent yields. Access to unsymmetrical diarylmethanes with this method is also explored and various factors are discussed. An aryl methyl ketone is used as the methylene donor to couple with two molecules of an aryl halide for the synthesis of various symmetric diarylmethanes under palladium catalysis. The mechanism involves a two-step coupling process in which the presence of a trace amount of H 2O is indispensable. The cross-coupling to unsymmetrical diarylmethanes with this method is also explored. Copyright
Catalytic asymmetric epoxidation
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Page/Page column 28, (2010/02/12)
The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.
