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Issue 60, 2016
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Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles

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Abstract

An unprecedented Ag(I)-catalyzed ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford heterocycles bearing both methylisoxazole and pyrrolidine moieties. The endo- and exo-cycloadducts were obtained in good yields with excellent stereoselectivities, assisted by tBu-Phosferrox and phosphoramidite as chiral ligands, respectively.

Graphical abstract: Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles

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Article information


Submitted
15 Apr 2016
Accepted
28 Jun 2016
First published
28 Jun 2016

Chem. Commun., 2016,52, 9458-9461
Article type
Communication

Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles

K. Liu, Y. Xiong, Z. Wang, H. Tao and C. Wang, Chem. Commun., 2016, 52, 9458
DOI: 10.1039/C6CC03169B

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