ORGLIST: Enantiomeric composition

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From: Jonas Nilsson (jonni$##$ifm.liu.se)
Date: Wed Apr 05 2000 - 07:54:29 EDT

Dear Orglist Members
I have an chiral compound which is based on the
1R,2R-trans-1,2-cyclopropanedicarboxylate. I need a good way to see if a
have got some racemization in this cyclopropane-ring.

I have optical rotation so the racemization is not complete at least. I
see no trace of the cis compound, probably due to it's more hindred
configuration. I might however have som of the other trans (1S,2S)
compound.

I was thinking about using the Eu(hfc)3 chiral NMR-shift ligand, which
we have inhouse. Has anybody any experience or good reference on this.
Most of what I seem to find is published in Journals we don't have. A
good reference or a review article would be great.

The cyclopropane-dicarboxylic acid is derivitized with one methyl ester
and one achiral amine. Would the Eu(hfc)3 shift the methyl ester protons
for instance? Can I use protic solvent with the Eu(hfc)3 (MeOH-d5). How
much of the shift-reagent should I use.

note Eh(hfc)3=Europium
tris[3-(heptafluoropropylhydroxymethylene)-(+)-camphorate] [CAS
34788-82-4]

Please Advise.

Sincerely
jN 

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