Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones. (10th October 2016)

• Record Type: Journal Article
• Authors: Cai, Yunfei; Tang, Yurong; Atodiresei, Iuliana; Rueping, Magnus
• Is Part Of: Angewandte Chemie. Volume 128:Number 45(2016)
• Page Start: 14332
• Page End: 14336
• Publication Date: 2016-10-10
• Subjects: Alkohole -- Brønsted-Säuren -- Organokatalyse -- Quartäre Stereozentren -- Umlagerungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201608023
• Languages: English
• ISSNs: 0044-8249

Abstract

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.