Work

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

Year: 2025

Type: article

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.

Source: Catalysts

DOI: 10.3390/catal15040393

Authors: Dong-Hua Xie, Yang Du, Da-Ming Du

Institution: Beijing Institute of Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,654

Funder: Beijing Institute of Technology