Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones. Issue 45 (10th October 2016)

• Record Type: Journal Article
• Authors: Cai, Yunfei; Tang, Yurong; Atodiresei, Iuliana; Rueping, Magnus
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 45(2016)
• Page Start: 14126
• Page End: 14130
• Publication Date: 2016-10-10
• Subjects: alcohols -- Brønsted acids -- organocatalysis -- quaternary stereocenters -- rearrangements; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201608023
• Languages: English
• ISSNs: 1433-7851

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. Abstract : A chiral Brønsted acid catalyzes the asymmetric Piancatelli rearrangement of a wide range of furylcarbinols with aniline derivatives, affording valuable 4‐aminocyclopentenones in high yields and with high enantio‐ and diastereocontrol. Challenging alkyl‐substituted tertiary furylcarbinols gave the corresponding products with a chiral quaternary stereocenter with excellent enantioselectivity.