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

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Discussion Overview

The discussion revolves around the possibility of changing the chirality of an atom, specifically focusing on the amino group attached to a chiral center. Participants explore various chemical strategies and reactions that might facilitate this change, including nucleophilic additions, stereochemical inversions, and electrolysis methods. The scope includes theoretical approaches and practical considerations in organic chemistry.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant proposes using nucleophilic addition to the carbonyl group while coordinating the amino group with a metal to induce a chirality change.
  • Another idea involves using an SN2 reaction to invert the stereochemistry, with uncertainty about how to temporarily remove a hydrogen to achieve a trigonal planar state.
  • A suggestion is made to convert the amino group to a double bond to make it achiral temporarily, allowing for potential control over the resulting stereochemistry.
  • A participant mentions the possibility of deprotecting the carboxyl group and conducting Kolbe electrolysis with controlled amounts of mono esterified oxalic acid to influence the product's dimerization.
  • Clarification is sought regarding whether the chirality in question refers to the carbon to which the amino group is attached.
  • One participant notes the existence of numerous papers on chiral synthesis, implying that literature may provide insights into the topic.
  • Another participant emphasizes the difficulty of providing advice without a complete understanding of the molecule and the specific goals of the modification.

Areas of Agreement / Disagreement

Participants express varying degrees of uncertainty and propose multiple competing methods for changing chirality. There is no consensus on a specific approach or solution, and the discussion remains unresolved.

Contextual Notes

Limitations include the lack of information about the entire molecular structure and the specific objectives of the modification, which may affect the feasibility of the proposed methods.

mycotheology
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Heres the chiral center:
eeee18ca8467ac59bfcf4241cc4f1bcd.png

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 here's 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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mycotheology said:
Heres the chiral center:
eeee18ca8467ac59bfcf4241cc4f1bcd.png

I want to change the chirality of the amino group.

You mean chirality of the carbon to which the amino group is attached?
 
If it is for an amino acid there are probably hundreds of papers out there that describe chiral synthesis.
 
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.
 
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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