139670-25-0Relevant academic research and scientific papers
Regio- and diastereoselective copper(I)-catalyzed allylic substitution of δ-hydroxy allylic chlorides by a silicon nucleophile
Hazra, Chinmoy K.,Irran, Elisabeth,Oestreich, Martin
, p. 4903 - 4908 (2013)
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
A novel palladium-catalyzed deoxygenation of enediols to 1,3-dienes
Trost,Tometzki
, p. 1235 - 1245 (2007/10/02)
Hydroxylative Knoevenagel condensation of aldehydes followed by reduction provides a simple entry to 1,4-enediols. Subjecting the dicarbonate to a palladium(0) catalyst in the presence of triisopropyl phosphite achieves a mild vinylogous deoxygenation to (E)-1,3-dienes. Stereocontrolled synthesis of the sex pheromone of the red bollworm moth, (E)-9,11-dodecadienyl acetate, and a formal synthesis of the cotton boll weevil antifeedant, α-eleostearic acid, demonstrate the utility of this new methodology.
