59935-64-7Relevant academic research and scientific papers
Electrophilic Cyclization of Phenylalkynediols to Naphthyl(aryl)iodonium Triflates with Chelating Hydroxyls: Preparation and X-ray Analyses
Hinkle, Robert J.,Bredenkamp, Sarah E.,Pike, Robert D.,Cheon, Seong Ik
, p. 11781 - 11786 (2017/11/24)
Alkynediols containing one propargylic alcohol as well as a second alcohol, which is propargylic or homopropargylic, react with PhI+CN-OTf (Stang's reagent) or 3,5-(CF3)2C6H3I+CN
Regio- and diastereoselective copper(I)-catalyzed allylic substitution of δ-hydroxy allylic chlorides by a silicon nucleophile
Hazra, Chinmoy K.,Irran, Elisabeth,Oestreich, Martin
supporting information, p. 4903 - 4908 (2013/08/23)
A perfectly γ-selective copper(I)-catalyzed allylic substitution of protected δ-hydroxy allylic chlorides with a silicon nucleophile generated by Si-B bond activation provides diastereoselective access to β-hydroxy α-chiral allylic silanes with an anti re
Synthesis of cyclic N-tosyliminocarbonates by Lewis acid catalyzed allylic substitution of trichloroacetimidates
Grigorjeva, Liene,Jirgensons, Aigars
supporting information, p. 5307 - 5316 (2012/10/30)
Allylic trichloroacetimidates bearing a δ-N-tosylcarbamoyloxy group were prepared in two steps from the corresponding diols, and their Bronsted and Lewis acid catalyzed cyclization reactions were investigated. It was found that N-tosylcarbamates derived from secondary and tertiary alcohols bearing alkyl substituents undergo a chemoselective allylic alkylation to give N-tosyliminocarbonates in good isolated yields. In turn, aryl-substituted substrates tend to give oxazolines by abstraction of the carbamate functionality. The cyclization of N-tosylcarbamates derived from secondary alcohols preferentially give trans-iminocarbonates. However, the trans selectivity varied and depended on the substitution pattern, configuration of the substrate, and the catalyst. A high trans selectivity could be achieved from (E) substrates by using TMSOTf as the catalyst. The synthetic utility of iminocarbonates was demonstrated by transforming them into 1,2-diols and cyclic carbonates as well as into N-tosyloxazolidinones by a halide ion-induced rearrangement. Copyright
Efficient synthesis of fluoren-9-ones by the palladium-catalyzed annulation of arynes by 2-haloarenecarboxaldehydes
Waldo, Jesse P.,Zhang, Xiaoxia,Shi, Feng,Larock, Richard C.
, p. 6679 - 6685 (2008/12/22)
(Chemical Equation Presented) Fluoren-9-ones and derivatives are readily prepared in good yields by the annulation of in situ generated arynes by 2-haloarenecarboxaldehydes in the presence of a palladium catalyst.
Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(I)-mediated reactions with dicyclohexylcarbodiimide
Duffy, Michael G.,Grayson, David H.
, p. 1555 - 1563 (2007/10/03)
(Z)-1,4-dihydroxyalk-2-enes were converted into 2,5-dihydrofurans and alkane-1,4-diols were converted into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas. The reaction involved protonation of the carbodiimide by acidic phenol followed by reaction with alkanol. Pd/CaCo3-quinoline catalyst system was employed in the presence of a little triethylamine to overcome partial hydrogenolysis.
