4412-78-6Relevant articles and documents
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).
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.
