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DOI: 10.1055/a-1938-1243
Organocatalytic Asymmetric Oxa-Michael–Michael Reaction of 3-Aryl-2-Nitroprop-2-Enols with Unsaturated Pyrazolones: Synthesis of Spirotetrahydropyranopyrazolones
This work was supported by MHRD-FAST programme (file no 22-3/2016-TS.II/TC) and DST-SERB (file no CRG/2018/001154). We also thank the Department of Biotechnology (DBT), Govt. of India (project no. BT/COE/34/SP28408/2018) for the provision of instrumental facilities.

Abstract
An organocatalytic asymmetric oxa-Michael–Michael reaction of 3-aryl-2-nitroprop-2-enols with alkylidene pyrazolones has been developed. This report describes the first use of a 3-aryl-2-nitroprop-2-enol as an O-nucleophile in enantioselective catalysis. With 10 mol% of a quinine-derived squaramide catalyst, a variety of spirotetrahydropyranopyrazolones were obtained in moderate yields, excellent diastereomeric ratios, and high to excellent enantioselectivities under mild reaction conditions.
Key Words
spiropyrazolones - oxa-Michael reaction - organocatalysis - asymmetric catalysis - enantioselectivity - cascade reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1938-1243.
- Supporting Information
Publication History
Received: 30 May 2021
Accepted after revision: 07 September 2021
Accepted Manuscript online:
07 September 2022
Article published online:
28 September 2022
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