Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement

Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement

Ring the changes: The first example of an intramolecular aza‐Piancatelli rearrangement is reported. Dysprosium(III) trifluoromethanesulfonate efficiently catalyzes the synthesis of functionalized azaspirocycles in a trans‐selective manner by a 4π electrocyclization of elaborated furylcarbinols (see...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-07, Vol.50 (31), p.7167-7170
Hauptverfasser: Palmer, Leoni I., Read de Alaniz, Javier
Format: Artikel
Sprache:eng
Schlagworte:
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
aza-Piancatelli
azaspirocycles
Catalysis
domino reactions
Dysprosium
Dysprosium - chemistry
lanthanides
rearrangement
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Zusammenfassung:Ring the changes: The first example of an intramolecular aza‐Piancatelli rearrangement is reported. Dysprosium(III) trifluoromethanesulfonate efficiently catalyzes the synthesis of functionalized azaspirocycles in a trans‐selective manner by a 4π electrocyclization of elaborated furylcarbinols (see scheme; Tf=trifluoromethanesulfonyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201102102