Synlett 2022; 33(05): 488-494
DOI: 10.1055/a-1747-2724
letter

Chiral Urea-Catalyzed Asymmetric Mannich Reaction of 3-Fluorooxindoles with α-Amidosulfones: Synthesis of Optically Active α-Fluoro-β-amino-oxindoles

Xin Zhang
,
Zhonglin Wei
,
Jungang Cao
,
Dapeng Liang
,
Yingjie Lin
,
Haifeng Duan
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.

Supporting Information



Publikationsverlauf

Eingereicht: 18. November 2021

Angenommen nach Revision: 20. Januar 2022

Accepted Manuscript online:
20. Januar 2022

Artikel online veröffentlicht:
09. Februar 2022

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