4412-78-6Relevant academic research and scientific papers
Rhodium-Catalyzed Asymmetric Cycloisomerization and Parallel Kinetic Resolution of Racemic Oxabicycles
Loh, Charles C. J.,Schmid, Matthias,Webster, Robert,Yen, Andy,Yazdi, Shabnam K.,Franke, Patrick T.,Lautens, Mark
, p. 10074 - 10078 (2016)
While desymmetrizations by intermolecular asymmetric ring-opening reactions of oxabicyclic alkenes with various nucleophiles have been reported over the past two decades, the demonstration of an intramolecular variant is unknown. Reported herein is the first rhodium-catalyzed asymmetric cycloisomerization of meso-oxabicyclic alkenes tethered to bridgehead nucleophiles, thus providing access to tricyclic scaffolds through a myriad of enantioselective C?O, C?N, and C?C bond formations. Moreover, we also demonstrate a unique parallel kinetic resolution, whereby racemic oxabicycles bearing two different bridgehead nucleophiles can be resolved enantioselectively.
Organocatalytic asymmetric Diels-Alder reaction of furan under high pressure
Mimoto, Akiko,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
scheme or table, p. 799 - 804 (2010/10/05)
A new method for the asymmetric Diels-Alder reaction between furan and acrolein has been developed through the combined use of chiral organocatalysts and high pressure (yield up to 91%; endo-adduct up to 19% ee, exo-adduct up to 26% ee).
A versatile and general one-pot method for synthesizing bis-spiroketal motifs
Georgiou, Thomas,Tofi, Maria,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
, p. 1945 - 1948 (2007/10/03)
A versatile and general method for the biomimetic construction of [5,5,5]- and [6,5,6]-bis-spiroketals, starting from easily accessible furan nuclei, by means of a powerful one-pot singlet oxygen-mediated cascade sequence is reported.
Combining two-directional synthesis and tandem reactions: Synthesis of trioxadispiroketals
McDermott, Paul J.,Stockman, Robert A.
, p. 27 - 29 (2007/10/03)
(Chemical Equation Presented) A tandem bromonium ion-promoted cyclization of two pendant hydroxyl groups onto a central furan core provides a highly direct route to both the [5,5,5]- and the [6,5,6]-trioxadispiroketal ring systems.
Tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization catalyzed by an organotungsten Lewis acid
Wang, Hsing-Shiun,Yu, Shuchun Joyce
, p. 1051 - 1055 (2007/10/03)
The tris(2-pyridyl)phosphine complex [P(2-py)3 W(CO)(NO)2](BF4)2 acts as a Lewis acid catalyst precursor for the tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization, which lead to the formation of a series of hyper-branched star polymers.
2,5-Disubstituted furans from acid catalyzed addition of α,β-enones to furan. Applications to the synthesis of C2-symmetric compounds
Cattalini, Marco,Cossu, Sergio,Fabris, Fabrizio,De Lucchi, Ottorino
, p. 637 - 647 (2007/10/03)
The scope of the double addition of α,β-unsaturated carbonyl compounds to furan has been investigated in water under acid catalysis. Two representative adducts (i.e. the ones to acrolein and 3-butenone 4a,b) subjected to Diels-Alder cycloaddition with a n
