Sie befinden Sich nicht im Netzwerk der Universität Paderborn. Der Zugriff auf elektronische Ressourcen ist gegebenenfalls nur via VPN oder Shibboleth (DFN-AAI) möglich. mehr Informationen...
Phosphine-catalyzed formal Buchner [6+1] annulation: construction of cycloheptatrienes
Ist Teil von
Chemical communications (Cambridge, England), 2023-11, Vol.59 (88), p.13215-13218
Erscheinungsjahr
2023
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
An unprecedented phosphine-catalyzed formal Buchner [6+1] annulation of a newly designed allenoate has been developed, providing a series of cycloheptatriene derivatives in moderate to good yields (up to 99%). This reaction demonstrates that the introduction of an electrophilic allylic group to allenoates effectively extends the reaction scope of phosphine-catalyzed annulation, providing a concise route to cycloheptatrienes. Mechanistic study indicated that this reaction involves a [4+2] Diels-Alder reaction and ring expansion of the bicyclo[4.1.0] moiety, which is similar to the Buchner reaction. Notably, an enantioselective variant of this [6+1] annulation can also be performed using a chiral iminophosphine catalyst.
A new method is developed to construct cycloheptatriene derivatives efficiently by phosphine-catalyzed formal Buchner [6+1] annulation of a newly designed allenoate and 4-oxo-4
H
-chromene-3-carbaldehydes.
Sprache
–
Identifikatoren
ISSN: 1359-7345
eISSN: 1364-548X
DOI: 10.1039/d3cc04905a
Titel-ID: cdi_rsc_primary_d3cc04905a
Format
–
Weiterführende Literatur
Empfehlungen zum selben Thema automatisch vorgeschlagen von bX