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Synthesis 2022; 54(09): 2213-2224
DOI: 10.1055/s-0041-1737804
DOI: 10.1055/s-0041-1737804
paper
Sc(OTf)3-Catalyzed [3+2]-Cycloaddition of Diazoacetoacetate Enones and N-Aryl Nitrones: Diastereoselective Synthesis of Functionalized Isoxazolidines with Three Contiguous Stereogenic Centers
This work was supported by the National Natural Science Foundation of China (21801198), the Wuhan Institute of Technology (17QD05), and the Graduate Innovation Fund of Wuhan Institute of Technology (CX2020280).
Abstract
A catalytic [3+2]-cycloaddition using Sc(OTf)3 as a Lewis acid catalyst is developed. This catalytic 1,3-dipolar cycloaddition diastereoselectively transforms diazoacetoacetate enones and N-aryl nitrones into highly functionalized isoxazolidines bearing three contiguous chiral centers. The feasibility of the uncatalyzed 1,3-dipolar cycloaddition is postulated by DFT calculations and substantiated experimentally.
Key words
Lewis acid catalysis - 1,3-dipolar cycloaddition - diazoacetoacetate enones - N-aryl nitrones - isoxazolidinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737804.
- Supporting Information
Publication History
Received: 23 November 2021
Accepted after revision: 14 December 2021
Article published online:
01 February 2022
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