Issue 24, 2018
From the journal:

Organic & Biomolecular Chemistry

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

Limin Yang, ORCID logo *a   Yunbo Lv,a   Fei Wanga  and  Guofu Zhong*a  

* Corresponding authors

a College of Materials, Chemistry & Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, China
E-mail: myang@hznu.edu.cn, zgf@hznu.edu.cn

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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Article information

DOI
https://doi.org/10.1039/C8OB00925B
Article type
Communication
Submitted
19 Apr 2018
Accepted
22 May 2018
First published
23 May 2018

Org. Biomol. Chem., 2018,16, 4433-4438

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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, 16, 4433 DOI: 10.1039/C8OB00925B

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