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Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones
Author(s) -
Cai Yunfei,
Tang Yurong,
Atodiresei Iuliana,
Rueping Magnus
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201608023
Subject(s) - cyclopentane , aniline , catalysis , brønsted–lowry acid–base theory , chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
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.