Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes

Meiyan Ni; Jianguo Zhang; Xiaoyu Liang; Yaojia Jiang; Teck Peng Loh

doi:10.1039/c7cc07178g

Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes

Meiyan Ni, Jianguo Zhang, Xiaoyu Liang, Yaojia Jiang^*, Teck Peng Loh

^*Corresponding author for this work

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

51 Citations (Scopus)

Abstract

An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from N-tosylhydrazones, followed by selective C-C bond cleavage of the cyclopropane ring, affords 1,4-ketoaldehyde derivatives in good to excellent yields. This method works with broad substrate scope and high regioselectivity.

Original language	English
Pages (from-to)	12286-12289
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	91
DOIs	https://doi.org/10.1039/c7cc07178g
Publication status	Published - 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from N-tosylhydrazones, followed by selective C-C bond cleavage of the cyclopropane ring, affords 1,4-ketoaldehyde derivatives in good to excellent yields. This method works with broad substrate scope and high regioselectivity.",

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AU - Liang, Xiaoyu

AU - Jiang, Yaojia

AU - Loh, Teck Peng

PY - 2017

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AB - An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from N-tosylhydrazones, followed by selective C-C bond cleavage of the cyclopropane ring, affords 1,4-ketoaldehyde derivatives in good to excellent yields. This method works with broad substrate scope and high regioselectivity.

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Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes

Abstract

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