61031-76-3Relevant articles and documents
Synthesis of a biofuel target through conventional organic chemistry
Page, Jordan P.,Robinson, Joshua W.,Albrecht, Karl O.,Cosimbescu, Lelia
supporting information, p. 1421 - 1423 (2018/03/07)
In this work, the biofuel target compound 2-ethyl-5,5-dimethylcyclopenta-1,3-diene (1) and its exo isomers (9a and 9b), were successfully synthesized via two different pathways from the common intermediate 4,4-dimethylcyclopent-2-ene-1-one (2). The first pathway produced the endocyclic product as a pure isomer via a triflate intermediate obtained from ketone 2 in 60% yield, followed by copper-catalyzed coupling with ethyl magnesium bromide in 63% yield. The second pathway employed a Grignard reaction with ketone 2, which generated an alcohol that was immediately subjected to mild acid-catalyzed elimination to yield primarily a mixture of exo isomers 9a and 9b in 46% yield. The preparation method developed by this work allowed for the production of a sufficient quantity of these targets to evaluate their fuel properties, which will be reported in a separate study.
Concise total syntheses of the bioactive mesotricyclic diterpenoids jatrophatrione and citlalitrione
Yang, Jiong,Long, Yun Oliver,Paquette, Leo A.
, p. 1567 - 1574 (2007/10/03)
The highly functionalized [5.9.5] tricyclic framework resident in jatrophatrione (1) and citlalitrione (2) has been synthesized. The route begins with the tandem anionic oxy-Cope rearrangement/methylation/transannular ene cyclization of 21 and subsequent introduction of a conjugated enone double bond. Hydroxyl-directed 1,4-reduction of this functionality in 25 with LiAlH4/Cul/hexamethylphosphoramide/tetrahydrofuran sets the stage for the implementation of a Grob fragmentation and expedited generation of 27. Stereocontrolled intramolecular hydrosilylation allows for the subsequent introduction of a cyclic carbonate as in 53. This intermediate undergoes remarkably efficient, fully regiocontrolled Treibs reaction to generate 54, with this maneuver serving as a pivotal step for making 1 available five steps later. Treatment of 1 with m-chloroperbenzoic acid leads to 2, with attack occurring preferentially on a α-face of the double bond more remote to the carbonyl.
EFFECTIVE CATALYTIC OXIDATION OF 1-ALKENES USING PALLADIUM-NITRO COMPLEXES IN THE PRESENCE OF AMIDES
Kiers, Niklaas H.,Feringa, Ben L.,Leeuwen, Piet W. N. M. van
, p. 2403 - 2406 (2007/10/02)
The rate of oxidation and the catalyst stability in the oxidation of 1-alkenes with O2 using as catalyst is considerably improved by the use of amides as ligands or solvents.