Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective tandem cyclic oxonium ylide formation and [2,3]-sigmatropic rearrangement from α-diazo-β-ketoester bearing cyclic allylic acetal functionality, providing the...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry letters 2009-05, Vol.38 (5), p.488-489
Hauptverfasser: Shimada, Naoyuki, Nakamura, Seiichi, Anada, Masahiro, Shiro, Motoo, Hashimoto, Shunichi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective tandem cyclic oxonium ylide formation and [2,3]-sigmatropic rearrangement from α-diazo-β-ketoester bearing cyclic allylic acetal functionality, providing the 2,8-dioxabicyclo[3.2.1]octane core structure of zaragozic acids in up to 93% ee.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2009.488