Squaramide-Catalyzed Three-Component Asymmetric [2 + 2 + 1] Cycloaddition Reaction Between 3-Hydroxy-1H-pyrrole-2,5-diones with Nitrosobenzene and Ethyl Diazoacetate

Dong Hua Xie; Yang Du; Da Ming Du

doi:10.3390/catal15040393

Squaramide-Catalyzed Three-Component Asymmetric [2 + 2 + 1] Cycloaddition Reaction Between 3-Hydroxy-1H-pyrrole-2,5-diones with Nitrosobenzene and Ethyl Diazoacetate

Dong Hua Xie, Yang Du, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

Abstract

An asymmetric [2 + 2 + 1] cycloaddition reaction between three-component 3-hydroxy-1H-pyrrole-2,5-diones, ethyl diazoacetate, and nitrosobenzene was successfully developed. A new series of chiral polysubstituted chiral isoxazolidinopyrrolidinediones with three consecutive stereocentres were obtained in up to 87% yield with up to >20:1 dr and 78% ee. In addition, a scaled-up synthesis was carried out, and a possible reaction mechanism was also proposed.

Original language	English
Article number	393
Journal	Catalysts
Volume	15
Issue number	4
DOIs	https://doi.org/10.3390/catal15040393
Publication status	Published - Apr 2025

Keywords

asymmetric catalysis
isoxazolidine
pyrrolidindione
squaramide

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title = "Squaramide-Catalyzed Three-Component Asymmetric [2 + 2 + 1] Cycloaddition Reaction Between 3-Hydroxy-1H-pyrrole-2,5-diones with Nitrosobenzene and Ethyl Diazoacetate",

abstract = "An asymmetric [2 + 2 + 1] cycloaddition reaction between three-component 3-hydroxy-1H-pyrrole-2,5-diones, ethyl diazoacetate, and nitrosobenzene was successfully developed. A new series of chiral polysubstituted chiral isoxazolidinopyrrolidinediones with three consecutive stereocentres were obtained in up to 87% yield with up to >20:1 dr and 78% ee. In addition, a scaled-up synthesis was carried out, and a possible reaction mechanism was also proposed.",

keywords = "asymmetric catalysis, isoxazolidine, pyrrolidindione, squaramide",

author = "Xie, {Dong Hua} and Yang Du and Du, {Da Ming}",

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year = "2025",

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doi = "10.3390/catal15040393",

language = "English",

volume = "15",

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T1 - Squaramide-Catalyzed Three-Component Asymmetric [2 + 2 + 1] Cycloaddition Reaction Between 3-Hydroxy-1H-pyrrole-2,5-diones with Nitrosobenzene and Ethyl Diazoacetate

AU - Xie, Dong Hua

AU - Du, Yang

AU - Du, Da Ming

PY - 2025/4

Y1 - 2025/4

N2 - An asymmetric [2 + 2 + 1] cycloaddition reaction between three-component 3-hydroxy-1H-pyrrole-2,5-diones, ethyl diazoacetate, and nitrosobenzene was successfully developed. A new series of chiral polysubstituted chiral isoxazolidinopyrrolidinediones with three consecutive stereocentres were obtained in up to 87% yield with up to >20:1 dr and 78% ee. In addition, a scaled-up synthesis was carried out, and a possible reaction mechanism was also proposed.

AB - An asymmetric [2 + 2 + 1] cycloaddition reaction between three-component 3-hydroxy-1H-pyrrole-2,5-diones, ethyl diazoacetate, and nitrosobenzene was successfully developed. A new series of chiral polysubstituted chiral isoxazolidinopyrrolidinediones with three consecutive stereocentres were obtained in up to 87% yield with up to >20:1 dr and 78% ee. In addition, a scaled-up synthesis was carried out, and a possible reaction mechanism was also proposed.

KW - asymmetric catalysis

KW - isoxazolidine

KW - pyrrolidindione

KW - squaramide

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DO - 10.3390/catal15040393

M3 - Article

AN - SCOPUS:105003560197

SN - 2073-4344

VL - 15

JO - Catalysts

JF - Catalysts

IS - 4

M1 - 393

ER -

Squaramide-Catalyzed Three-Component Asymmetric [2 + 2 + 1] Cycloaddition Reaction Between 3-Hydroxy-1H-pyrrole-2,5-diones with Nitrosobenzene and Ethyl Diazoacetate

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Keywords

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