- Rhodium-Catalyzed Asymmetric Cycloisomerization and Parallel Kinetic Resolution of Racemic Oxabicycles
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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.
- Loh, Charles C. J.,Schmid, Matthias,Webster, Robert,Yen, Andy,Yazdi, Shabnam K.,Franke, Patrick T.,Lautens, Mark
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- Organocatalytic asymmetric Diels-Alder reaction of furan under high pressure
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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).
- Mimoto, Akiko,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
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scheme or table
p. 799 - 804
(2010/10/05)
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- A versatile and general one-pot method for synthesizing bis-spiroketal motifs
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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.
- Georgiou, Thomas,Tofi, Maria,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
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p. 1945 - 1948
(2007/10/03)
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- Combining two-directional synthesis and tandem reactions: Synthesis of trioxadispiroketals
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(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.
- McDermott, Paul J.,Stockman, Robert A.
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- Tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization catalyzed by an organotungsten Lewis acid
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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.
- Wang, Hsing-Shiun,Yu, Shuchun Joyce
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p. 1051 - 1055
(2007/10/03)
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- 2,5-Disubstituted furans from acid catalyzed addition of α,β-enones to furan. Applications to the synthesis of C2-symmetric compounds
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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
- Cattalini, Marco,Cossu, Sergio,Fabris, Fabrizio,De Lucchi, Ottorino
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p. 637 - 647
(2007/10/03)
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