feel like I need to change up the _Organic Syntheses_ roulette in some way that's more likely to give me older results. right now it skews towards new syntheses too much. hm...let's try random 4-digit number instead
searching orgsyn.org on "1323"
and the first hit is
http://orgsyn.org/demo.aspx?prep=v92p0213
now this is a fascinating one, if special-purpose again. the goal is *stereoselective* hydrogenation of substituted quinolines to 1,2,3,4-tetrahydroquinolines
and once you get the catalyst made, it's used to hydrogenate quinaldine (2-methylquinoline) to (S)-2-methyl-1,2,3,4-tetrahydroquinoline, in 94% enantiomeric excess, by hydrogenation at 50 atm pressure of hydrogen gas in a solvent of methanol spiked with trifluoroacetic acid, probably to insure protonation of the quinaldine (I suspect that without it you might get the 1,4-dihydroquinoline instead)
neat, I guess? nothing I can see wanting to do any time soon. who has iridium lying around
ordinary hydrogenation of aromatic rings is going to yield racemic products but stereoselective hydrogenation is here achieved with a bespoke chiral organoriridium catalyst. most of the synthetic procedure describes how to make that catalyst starting from (1S,2S)-1,2-diphenylethylenediamine. again, a vicinal diamine serves as a building block for a chiral ligand stuck on a transition metal
pentamethylcyclopentadienyliridium(III) dichloride dimer serves as the iridium source for the synthesis