Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones

Yunfei Cai, Yurong Tang, Iuliana Atodiresei, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)14126-14130
Number of pages5
JournalAngewandte Chemie International Edition
Volume55
Issue number45
DOIs
StatePublished - Oct 10 2016

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