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

Yunfei Cai; Yurong Tang; Iuliana Atodiresei; Magnus Rueping

doi:10.1002/anie.201608023

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 journal › Article › peer-review

67 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 language	English (US)
Pages (from-to)	14126-14130
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	45
DOIs	https://doi.org/10.1002/anie.201608023 https://doi.org/10.1002/ange.201608023
State	Published - Oct 10 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.

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title = "Catalytic Asymmetric Piancatelli Rearrangement: Br{\o}nsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones",

abstract = "The first catalytic asymmetric Piancatelli reaction is reported. Catalyzed by a chiral Br{\o}nsted 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.",

author = "Yunfei Cai and Yurong Tang and Iuliana Atodiresei and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.",

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T1 - Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones

AU - Cai, Yunfei

AU - Tang, Yurong

AU - Atodiresei, Iuliana

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.

PY - 2016/10/10

Y1 - 2016/10/10

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/623161

UR - http://onlinelibrary.wiley.com/doi/10.1002/anie.201608023/abstract

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DO - 10.1002/anie.201608023

M3 - Article

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EP - 14130

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 45

ER -

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

Abstract

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