Synonyms:N-fluorosuccinimide;2,5-Pyrrolidinedione,1-fluoro;
The study focuses on the enantioselective synthesis of a,a-chlorofluoro carbonyl compounds from simple aldehydes or ketones, which can be further transformed into various optically active molecules with fluorinated quaternary carbon centers through nucleophilic substitution. The researchers used racemic a-chloroaldehydes as precursors and synthesized a,a-chlorofluoro aldehydes with high enantioselectivity using N-fluorosuccinimide (NFSI) and an organocatalyst developed by J?rgensen et al. These enantioenriched compounds were then converted into unsymmetrical a,a-chlorofluoro ketones. The study also explored the direct synthesis of a,a-chlorofluoro ketones from a-unsubstituted ketones using chiral a,a-dichloromalonate. The synthesized compounds were successfully subjected to nucleophilic substitution reactions with sodium azide or thiols, yielding the corresponding substituted products without loss of optical purity.
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