Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones
KAUST DepartmentKAUST Catalysis Center (KCC)
MetadataShow full item record
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.