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Updated: Mar 11, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates
Lijun Zhang1, Wenzhong Zhang1, Haibo Mei1
1School of Chemistry and Chemical Engineering, State Key laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China. hanjl@nju.edu.cn.
Abstract:
Reported herein is a Cu(i)/bisoxazoline ligand-catalyzed aldol reaction of unprotected tertiary enolates generated in situ from 3-(1,1-dihydroxy-2,2,2-trifluoroethyl)-substituted derivatives of 3-fluoro-2-oxindoles. A range of α-fluoro-β-aryl/hetaryl/alkyl-β-hydroxy-indolin-2-ones containing C-F quaternary stereogenic centers of high pharmaceutical importance were furnished in good yields and satisfactory diastereo- and enantioselectivities. The reactions were conducted under operationally convenient conditions and displayed wide substrate/functional group generality including unprotected N-H on the tertiary enolates, and aromatic, hetero-aromatic and aliphatic aldehydes.
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