title: Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones.
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.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Cai
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Yurong
authors.initials: Y
authors.lastname: Tang
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Iuliana
authors.initials: I
authors.lastname: Atodiresei
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany. Magnus.Rueping@rwth-aachen.de.|King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC), Thuwal, 23955-6900, Saudi Arabia. Magnus.Rueping@rwth-aachen.de.
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
keywords: Brønsted acids; alcohols; organocatalysis; quaternary stereocenters; rearrangements