Enantioselective Synthesis of 1-Ferrocenylalkylamines via 1,2-Addition of Organolithium Compounds to Ferrocenecarboxaldehyde-SAMP-Hydrazone

Asymmetric Synthesis of PlanarChiral 2-Monosubstituted Diferrocenyl Ketones

“…Ozonolysis in dichloromethane at -78°C led to the corresponding ketone 4b in 21% yield, but decomposition was observed. Although ozonolysis turned out to be a very efficient method to cleave various ferrocenyl-SAMP-hydrazones, [6][7][8][9][10][11][12][13] in the present case this method is not practicable. So far the cleavage of the phosphinylated diferrocenyl ketones was not successful, because all attempts led to decomposition.…”

Efficient Asymmetric Synthesis of Planar‐Chiral Bisferrocenes

“…The reaction mixture was then treated with AlCl 3 (12 mg, 0.09 mmol). The (12). HRMS (EI + ): C 23 H 24 Fe 2 S 2 : calcd.…”

“…[11] Previous work in our laboratory has been focused on the asymmetric synthesis of chiral ferrocenyl ligands using the SAMP/RAMP-hydrazone methodology and exploring their use in catalytic asymmetric synthesis. [12] More recently this method was extended to bisferrocenes whereby valuable monosubstituted diferrocenyl ketones 6 could be efficiently synthesized. [12j] We envisioned that this procedure could be further elaborated into a synthesis of disubstituted diferrocenyl ketones 7 (Figure 2).…”

Asymmetric processes

“…45 Two different strategies for the addition to the C᎐ ᎐ N bond of hydrazones are represented by the addition of organolithium reagents to SAMP hydrazones of ferrocene aldehydes 34 in у98% de, 46 where the auxiliary is on the nitrogen atom of the hydrazone, and secondly, addition to a dimethylhydrazone of glyoxal 35, 47 where the auxiliary is a chiral aminal formed on the second aldehyde group.…”