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Updated: Jun 13, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Enantioselective Mannich Reaction between Cyclic N-Sulfonyl Ketimines and Isatin-Derived Ketimines
Yao-Yao Mei1, Chong-Xiao Xu1, Feng Sha1
1Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
Abstract:
An enantioselective Mannich reaction with cyclic N-sulfonyl ketimines as the nucleophiles was developed. In the presence of 5 mol % chiral thiourea catalyst C11, the asymmetric Mannich reaction between cyclic N-sulfonyl ketimines and isatin-derived ketimines was achieved in high yields and good-to-excellent enantioselectivities (84-99% yields with 75-99.8% ee). This methodology provided an effective route to construct chiral 3-amino-2-oxindoles containing a cyclic N-sulfonyl ketimine scaffold. The initial biological evaluation of the products in cell-based assays demonstrated that some compounds have excellent antiproliferative activity against human osteosarcoma cells.
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