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Asymmetric Catalytic [4+5] Annulation of ortho‐Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement
Ist Teil von
Chemistry : a European journal, 2020-03, Vol.26 (17), p.3803-3809
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2020
Link zum Volltext
Quelle
Wiley Online Library
Beschreibungen/Notizen
Palladium‐catalyzed asymmetric [4+5] annulation of ortho‐quinone methides (o‐QMs) with substituted vinylethylene carbonates (VECs) is described for the first time, giving a novel enantioselective approach to chiral nine‐membered benzoheterocycles. Based on this designed [4+5] annulation, an unprecedented silica gel‐promoted tandem rearrangement reaction featuring a unique asymmetric aromatic Claisen rearrangement is explored at room temperature, offering a new method for asymmetric construction of all‐carbon quaternary stereocenters embedded in chiral functionalized homoallylic alcohols.
Asymmetric annulation: With the development of a novel Pd‐catalyzed asymmetric [4+5] annulation of ortho‐quinone methides (o‐QMs) with vinylethylene carbonates (VECs), an unprecedented tandem rearrangement reaction featuring a unique asymmetric aromatic Claisen rearrangement is described. This study enables not only enantioselective access to chiral medium‐sized benzoheterocycles, but also gives a new asymmetric method for constructing all‐carbon quaternary stereocenters contained in chiral functionalized homoallylic alcohols.