AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

Longyun Lyu; Han Xie; Huaixue Mu; Qijie He; Zhaoxiang Bian; Jun Wang

doi:10.1039/c5qo00106d

AlCl₃-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

Longyun Lyu, Han Xie, Huaixue Mu, Qijie He, Zhaoxiang Bian^*, Jun Wang^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

6 Citations (Scopus)

Abstract

The inexpensive Lewis acid AlCl₃ was found to be an efficient catalyst for the O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and alcohols. Instead of carboxylic acid in the classical Passerini reaction, alcohols performed both as the solvent and substrate nicely to afford α-alkoxy-amide products in good yield (up to 91%). This method provides practical access for functional α-alkoxy-β,γ-enamide derivatives.

Original language	English
Pages (from-to)	815-818
Number of pages	4
Journal	Organic Chemistry Frontiers
Volume	2
Issue number	7
DOIs	https://doi.org/10.1039/c5qo00106d
Publication status	Published - Jul 2015

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title = "AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides",

abstract = "The inexpensive Lewis acid AlCl3 was found to be an efficient catalyst for the O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and alcohols. Instead of carboxylic acid in the classical Passerini reaction, alcohols performed both as the solvent and substrate nicely to afford α-alkoxy-amide products in good yield (up to 91%). This method provides practical access for functional α-alkoxy-β,γ-enamide derivatives.",

author = "Longyun Lyu and Han Xie and Huaixue Mu and Qijie He and Zhaoxiang Bian and Jun Wang",

note = "We gratefully thank the start-up fund from the South University of Science and Technology of China (SUSTC) for financial support.",

year = "2015",

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doi = "10.1039/c5qo00106d",

language = "English",

volume = "2",

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journal = "Organic Chemistry Frontiers",

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publisher = "Royal Society of Chemistry",

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T1 - AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

AU - Lyu, Longyun

AU - Xie, Han

AU - Mu, Huaixue

AU - He, Qijie

AU - Bian, Zhaoxiang

AU - Wang, Jun

N1 - We gratefully thank the start-up fund from the South University of Science and Technology of China (SUSTC) for financial support.

PY - 2015/7

Y1 - 2015/7

N2 - The inexpensive Lewis acid AlCl3 was found to be an efficient catalyst for the O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and alcohols. Instead of carboxylic acid in the classical Passerini reaction, alcohols performed both as the solvent and substrate nicely to afford α-alkoxy-amide products in good yield (up to 91%). This method provides practical access for functional α-alkoxy-β,γ-enamide derivatives.

AB - The inexpensive Lewis acid AlCl3 was found to be an efficient catalyst for the O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and alcohols. Instead of carboxylic acid in the classical Passerini reaction, alcohols performed both as the solvent and substrate nicely to afford α-alkoxy-amide products in good yield (up to 91%). This method provides practical access for functional α-alkoxy-β,γ-enamide derivatives.

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DO - 10.1039/c5qo00106d

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AN - SCOPUS:84941775363

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JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 7

ER -

AlCl₃-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

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