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- Title
Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones.
- Authors
Cai, Yunfei; Tang, Yurong; Atodiresei, Iuliana; Rueping, Magnus
- Abstract
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.
- Subjects
REARRANGEMENTS (Chemistry); BRONSTED acids; ELECTROCYCLIC reactions (Chemistry); CYCLOPENTENONE synthesis; ANILINE derivatives; ENANTIOSELECTIVE catalysis
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 45, p14126
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201608023