Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions

Xingxing Wu; Bin Liu; Yuexia Zhang; Martin Jeret; Honglin Wang; Pengcheng Zheng; Song Yang; Bao An Song; Yonggui Robin Chi

doi:10.1002/anie.201606571

Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions

Xingxing Wu, Bin Liu, Yuexia Zhang, Martin Jeret, Honglin Wang, Pengcheng Zheng, Song Yang^*, Bao An Song, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

77 Citations (Scopus)

Abstract

An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β³-amino-acid derivatives.

Original language	English
Pages (from-to)	12280-12284
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	40
DOIs	https://doi.org/10.1002/anie.201606571
Publication status	Published - Sept 26 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

cycloaddition
heterocycles
N-heterocyclic carbene
organocatalysis
reaction mechanisms

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10.1002/anie.201606571

Cite this

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title = "Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions",

abstract = "An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives.",

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doi = "10.1002/anie.201606571",

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T1 - Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals

T2 - Carbene-Catalyzed Formal [3+2] Reactions

AU - Wu, Xingxing

AU - Liu, Bin

AU - Zhang, Yuexia

AU - Jeret, Martin

AU - Wang, Honglin

AU - Zheng, Pengcheng

AU - Yang, Song

AU - Song, Bao An

AU - Chi, Yonggui Robin

PY - 2016/9/26

Y1 - 2016/9/26

N2 - An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives.

AB - An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives.

KW - cycloaddition

KW - heterocycles

KW - N-heterocyclic carbene

KW - organocatalysis

KW - reaction mechanisms

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JF - Angewandte Chemie - International Edition

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ER -

Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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