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DOI: 10.1055/a-1747-2724
Chiral Urea-Catalyzed Asymmetric Mannich Reaction of 3-Fluorooxindoles with α-Amidosulfones: Synthesis of Optically Active α-Fluoro-β-amino-oxindoles
We thank the financial support from the National Natural Science Foundation of China (Grant No. 51373067).
Abstract
The asymmetric Mannich reaction of 3-fluorooxindoles and α-amidosulfones catalyzed by a chiral urea catalyst derived from quinine in presence of K3PO4 was developed. Through the asymmetric reaction, a series of α-fluoro-β-amino-oxindoles, containing a tertiary carbon stereocenter, could be obtained in high yields (up to 95%) with high enantioselectivity (95%) and diastereoselectivity (>99:1). Such α-fluoro-β-amino-oxindole compounds are expected to become candidates in the field of medicine.
Key words
Mannich reaction - 3-fluorooxindoles - α-fluoro-β-amino-oxindoles - quinine-derived skeleton - urea-catalyzed catalystsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1747-2724.
- Supporting Information
Publication History
Received: 18 November 2021
Accepted after revision: 20 January 2022
Accepted Manuscript online:
20 January 2022
Article published online:
09 February 2022
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