Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

Jie Chen; Pan Guo; Jianguo Zhang; Jiaxin Rong; Wangbin Sun; Yaojia Jiang; Teck Peng Loh

doi:10.1002/anie.201906213

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

Jie Chen, Pan Guo, Jianguo Zhang, Jiaxin Rong, Wangbin Sun, Yaojia Jiang^*, Teck Peng Loh

^*Corresponding author for this work

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

55 Citations (Scopus)

Abstract

An efficient Rh^II-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C−C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

Original language	English
Pages (from-to)	12674-12679
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	36
DOIs	https://doi.org/10.1002/anie.201906213
Publication status	Published - Sept 2 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

carbene chemistry
enaminones
ruthenium
synthetic methods
α-vinyl aldehydes

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10.1002/anie.201906213

Cite this

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abstract = "An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C−C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.",

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T1 - Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

AU - Chen, Jie

AU - Guo, Pan

AU - Zhang, Jianguo

AU - Rong, Jiaxin

AU - Sun, Wangbin

AU - Jiang, Yaojia

AU - Loh, Teck Peng

PY - 2019/9/2

Y1 - 2019/9/2

N2 - An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C−C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

AB - An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C−C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

KW - carbene chemistry

KW - enaminones

KW - ruthenium

KW - synthetic methods

KW - α-vinyl aldehydes

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JO - Angewandte Chemie - International Edition

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Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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