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Is it possible to change the chirality of an atom like this?

by mycotheology
Tags: atom, chirality
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mycotheology
#1
Oct22-13, 01:26 PM
P: 90
Heres the chiral center:

I want to change the chirality of the amino group. I was wondering if I can do it through some kind of nucleuphilic addition to the carbonyl group, while adding something to adding a metal that will coordinate the amino group and drag it back or force it to change chirality or something like that.

Another idea I had was to use some kind of SN2 to invert the stereochemistry, but I have no idea how to do that. Is there any way I can remove a hydrogen from that chiral center in order to temporarily turn it trigonal planar, then when I re-hydrogenate it, at least I'd have a racemate.

Or would it be possible to tenporarily make the amino group achiral by converting it to a double bond or something? Then when its trigonal planar, I suppose I could figure out how to get the right stereochemistry.

Or heres another idea, maybe I could deprotect the carboxyl group, then run a kolbe electrolysis on it, but I will put an excess of mono esterified oxalic acid so that the majority of the my product will dimerise with the oxalic acid, rather than itself. Only problem there, is the oxalic acid will dimerise with itself, but I suppose I could add tiny amounts of the oxalic acid in at a time. This seems like it just might work.

Any ideas?
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Borek
#2
Oct22-13, 02:54 PM
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P: 23,599
Quote Quote by mycotheology View Post
Heres the chiral center:

I want to change the chirality of the amino group.
You mean chirality of the carbon to which the amino group is attached?
gravenewworld
#3
Oct22-13, 05:51 PM
P: 1,408
If it is for an amino acid there are probably hundreds of papers out there that describe chiral synthesis.

mycotheology
#4
Oct23-13, 05:32 AM
P: 90
Is it possible to change the chirality of an atom like this?

Yeah I meant chirality of the carbon. No, its not for an amino acid and synthesising it isn't an option in this case, I need to find a way to modify it.
gravenewworld
#5
Oct23-13, 08:27 AM
P: 1,408
There may be ways but it is hard to give advice without seeing the whole molecule and knowing what you are really trying to do.


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