Issue 13, 2022

Asymmetric 1,3-dipolar cycloaddition of 4-amino pyrazolone-based azomethine ylides: a straightforward approach to spiropyrazolones

Abstract

The asymmetric [3 + 2] cycloaddition of 4-amino pyrazolone-derived azomethine ylides with α,β-enones has been established for the synthesis of 4-spiropyrazolones derivatives with four contiguous stereocenters. This cycloaddition process delivered spiro[pyrrolidine-2,4′-pyrazolone] derivatives in high yields with excellent stereoselectivities (up to 95% yields, >20 : 1 dr and >99% ee) under mild conditions.

Graphical abstract: Asymmetric 1,3-dipolar cycloaddition of 4-amino pyrazolone-based azomethine ylides: a straightforward approach to spiropyrazolones

Supplementary files

Article information

Article type
Research Article
Submitted
15 Mar 2022
Accepted
19 May 2022
First published
21 May 2022

Org. Chem. Front., 2022,9, 3585-3590

Asymmetric 1,3-dipolar cycloaddition of 4-amino pyrazolone-based azomethine ylides: a straightforward approach to spiropyrazolones

Y. Huang, X. Wei, X. Bao, S. Nawaz, J. Qu and B. Wang, Org. Chem. Front., 2022, 9, 3585 DOI: 10.1039/D2QO00426G

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