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Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones

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Abstract

A chiral N-heterocyclic carbene (NHC)-catalyzed 1,3-dipolar [3 + 2] cycloaddition reaction of 3-oxopyrazolidin-1-ium-2-ides and α-chloroaldehydes was developed for the synthesis of pyrazolo[1,2-a]pyrazole-1,7-diones in moderate to good yields (up to 76%) with good enantioselectivities (up to 98% ee) and diastereoselectivities (up to 8 : 1 dr).

Graphical abstract: Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones

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Publication details

The article was received on 19 Apr 2018, accepted on 22 May 2018 and first published on 23 May 2018


Article type: Communication
DOI: 10.1039/C8OB00925B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones

    L. Yang, Y. Lv, F. Wang and G. Zhong, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00925B

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