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Synthesis of 2-fluoro-2-pyrrolines via tandem reaction of α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates†
Jieru Yang,Xiaofan Zhou,Yu Zeng,Chaoqian Huang,Yuanjing Xiao
Chemical Communications Pub Date : 03/07/2016 00:00:00 , DOI:10.1039/C6CC00831C
Abstract

A simple base-mediated tandem SN2′/SNV reaction of the readily available α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates was developed, which provide an efficient access to functionalized tetrasubstituted 2-fluoro-2-pyrrolines in good to excellent yields. In contrast, simple 1,2-nucleophilic adducts were produced when α-trifluoromethyl styrenes were used.

Graphical abstract: Synthesis of 2-fluoro-2-pyrrolines via tandem reaction of α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates
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