Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones
Type
ArticleKAUST Department
Chemical Science ProgramKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2016-10-10Online Publication Date
2016-10-10Print Publication Date
2016-11-02Permanent link to this record
http://hdl.handle.net/10754/623161
Metadata
Show full item recordAbstract
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.Citation
Cai 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.Sponsors
Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.Publisher
WileyJournal
Angewandte ChemieAdditional Links
http://onlinelibrary.wiley.com/doi/10.1002/anie.201608023/abstractae974a485f413a2113503eed53cd6c53
10.1002/anie.201608023