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

Handle URI:
http://hdl.handle.net/10754/623161
Title:
Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones
Authors:
Cai, Yunfei; Tang, Yurong; Atodiresei, Iuliana; Rueping, Magnus ( 0000-0003-4580-5227 )
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.
KAUST Department:
KAUST Catalysis Center (KCC)
Citation:
Cai Y, Tang Y, Atodiresei I, Rueping M (2016) Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones. Angewandte Chemie International Edition 55: 14126–14130. Available: http://dx.doi.org/10.1002/anie.201608023.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
13-Oct-2016
DOI:
10.1002/anie.201608023; 10.1002/ange.201608023
Type:
Article
ISSN:
1433-7851
Sponsors:
Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/anie.201608023/abstract
Appears in Collections:
Articles; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorCai, Yunfeien
dc.contributor.authorTang, Yurongen
dc.contributor.authorAtodiresei, Iulianaen
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2017-04-13T11:50:58Z-
dc.date.available2017-04-13T11:50:58Z-
dc.date.issued2016-10-13en
dc.identifier.citationCai Y, Tang Y, Atodiresei I, Rueping M (2016) Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones. Angewandte Chemie International Edition 55: 14126–14130. Available: http://dx.doi.org/10.1002/anie.201608023.en
dc.identifier.issn1433-7851en
dc.identifier.doi10.1002/anie.201608023en
dc.identifier.doi10.1002/ange.201608023en
dc.identifier.urihttp://hdl.handle.net/10754/623161-
dc.description.abstractThe 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.en
dc.description.sponsorshipY.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/anie.201608023/abstracten
dc.subjectalcoholsen
dc.subjectBrønsted acidsen
dc.subjectorganocatalysisen
dc.subjectquaternary stereocentersen
dc.subjectrearrangementsen
dc.titleCatalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenonesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University Landoltweg1,52074 Aachen (Germany)en
kaust.authorRueping, Magnusen
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