Synthesis Of 2-Fluoro-2-Pyrrolines Via Tandem Reaction Of Alpha-Trifluoromethyl-Alpha,Beta-Unsaturated Carbonyl Compounds With N-Tosylated 2-Aminomalonates

A simple base-mediated tandem S(N)2'/SNV reaction of the readily available alpha-trifluoromethyl-alpha,beta-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 alpha-trifluoromethyl styrenes were used.