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Quaternary alpha-fluoro carbonyl compounds were produced from electrophilic asymmetric fluorination of tertiary enolates by N-fluoro-2,10-camphorsultams in moderate yield and enatiomeric excess. These reagents displayed a sense of asymmetric induction that is in contrast with that for (camphorylsulfonyl)oxaziridine hydroxylating reagents, a closely related compound. The fluorination of the sodium enolate of 2-methyl-1-tetralone by (-)-N-fluoro-2,10-(3,3-dichlorocamphorsusltam) exhibited the highest asymmetric induction.

The enantioselective synthesis of epimerizable alpha-fluoro aldehydes and their use as chiral building blocks through the asymmetric synthesis of 4-deoxy-4-fluor-D-arabinopyranose, is reported. Fluorinated carbohydrates are of particular interest due to their significant biological activity, and their usefulness as probes of biochemical mechanisms.

Two approaches toward photochemical asymmetric synthesis are described. The first approach involves the use of modified zeolites as 'microreactors' and the second approach involves the use of optically active ammonium ions as ionic chiral auxiliaries. An evaluation of the efficiency of the two methods showed that the approach utilizing zeolite, while potentially more versatile, results in lower optical yields.