Re: ORGLIST: Problems determining product stereochemistry

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From: ling huang (ling.huang$##$prodigy.net)
Date: Mon Jul 07 2008 - 14:35:12 EDT


Hi Lawrence,
                      Have you considered using XRay -crystallography. If your product is a solid or can be made into a solid derivative then this could be considered. It has to be in crystal form. Sorry this may be a too simple an answer.
   
  Ling
   
  Ling Huang
  Chemistry Department
  Sacramento City College
  http://www.freewebs.com/huangl24
  http://www.scc.losrios.edu
  

Lawrence Milo <tazmusica2$##$gmail.com> wrote:
  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.
Sincerely,
Lawrence Milo

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