The 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.
Bibliographical noteKAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.