ORGLIST: Problems determining product stereochemistry

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From: Lawrence Milo (tazmusica2$##$
Date: Wed Jul 02 2008 - 12:59:17 EDT

Dear Orglist members,
I am a graduate student at Tufts University. I have been searching the
literature for methods to determine the absolute stereochemistry of a
product from a particular reaction. The structure of the product is included
as a picture attachment (. When the reaction is run in D2O, a deuterium (in
red) is placed at the carbon labeled "A", and when run in H2O, a proton is
placed there. This is supported by NMR data and LC/MS data. The NMR data
seem to suggest a stereospecific placement of the deuterium (or proton,
depending on the conditions), however the absolute stereochemistry is
unknown. Are there any methods (e.g. specific chiral shift reagents) that I
can use to 1) confirm that the placement of the deuterium/proton is indeed
stereospecific (that the product mixture is not racemic), and 2) determine
the absolute stereochemistry at that center (carbon "A"). Thank you for your
help in advance.
Lawrence Milo


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