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Ketamine salts solubility

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OK, I'm begging again:

https://doi.org/10.1021/acs.joc.8b01673

Direct N-H/N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

Just so people realise, I AM aware that the quality of many papers of Indian origin are very dubious. Anyone else remember the fake '1-pot synthesis of fentanyl' that was someone's pHd work (and got retracted since it was made up) BUT:

1)This is published in the JOC, a high impact journal.
2)The researchers have worked on several papers on aziridines so it seems they have developed a knowledge bade.
3)They cite and are cited appropriately and not just other people within their own department (a la Jan Hendrik Schön AKA Nobel Scandal)
4)A totally different team developed a related approach (N-phenoxy) while they use an animoxy

So why the hassle?

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OK, so you likely wonder what the heck is the point of THAT? Well, it's because that 3-membered ring is under a lot of strain and so it will ring-open to an alkanolamine or an aminoester or an aminoketone or an aminoalkylsulfonate or... well MANY things. What is even better is that the ring-opening will be almost 100% trans. I mean 99.8% ee or better (i.e. >99.9% trans)

Now, if one were to apply it to say (a ring-substituted) propenylbenzene, you could produce optically pure (ring-substituted) pseudoephedrine. I just use those as examples. I do not see any advantage in that since IF you wanted those, it's only of great benefit when the precursors are costly.


BTW the catalyst for THIS reaction is Bis[rhodium(α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid)]. The catalyst costs £400/gram so you can see it's only when the precursor is EXPENSIVE. It is actually a very interesting example of how a catalyst works. When you get that far down the periodic table, you can get some wacky oxidation states. Rh can be +1, +2, +3, +4, +5, +6 and the catalyst has a LOT of steric bulk and so it works by promoting an electron (HOMO/LUMO theory).

It get's VERY complex. I am hoping that their will be alternatives BUT I need the article to test.
 
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