Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones
KAUST DepartmentChemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2016-10-10
Print Publication Date2016-11-02
Permanent link to this recordhttp://hdl.handle.net/10754/623161
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AbstractThe first catalytic asymmetric Piancatelli reaction is reported. Catalyzed by a chiral Brønsted acid, the rearrangement of a wide range of furylcarbinols with a series of aniline derivatives provides valuable aminocyclopentenones in high yields as well as excellent enantioselectivities and diastereoselectivities. The high value of the aza-Piancatelli rearrangement was demonstrated by the synthesis of a cyclopentane-based hNK1 antagonist analogue.
CitationCai Y, Tang Y, Atodiresei I, Rueping M (2016) Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones. Angewandte Chemie International Edition 55: 14126–14130. Available: http://dx.doi.org/10.1002/anie.201608023.
SponsorsY.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.