1036244-24-2Relevant academic research and scientific papers
The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction
Rehman, Mintu,Surendran, Sravya,Siddavatam, Nagendra,Rajendar, Goreti
, p. 329 - 333 (2022/01/20)
Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.
Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B
Dussart, Nicolas,Trinh, Huu Vinh,Gueyrard, David
supporting information, p. 4790 - 4793 (2016/10/14)
The preparation of exo-enol esters from cyclic anhydrides is reported using a modified Julia olefination. The reaction is highly stereoselective. The Smiles rearrangement can be performed in a one-pot process, giving a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones, and this methodology was applied to the synthesis of maculalactone B.
Total synthesis of artochamins F, H, I, and J through cascade reactions
Nicolaou,Lister, Troy,Denton, Ross M.,Gelin, Christine F.
, p. 4736 - 4757 (2008/09/21)
A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] cycloaddition
