ORGLIST:RE: Mitsunobu Rxn & Fmoc

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From: Christopher Joseph Gorman (cjgorman$##$
Date: Thu Jul 22 2004 - 17:09:17 EDT


Having some of any tri-substituted amine in solution should make the whole
work. Here's why:

 (such as triethylamine, or pyridine) work, because Fmoc doesn't move generally
so long as the whole pot is overall kept at least somewhat basic -- and the
tri-substituted amine nucleophilic addition side reaction won't compete with
adding to the phosphorus (not irreversibly) -- If you look up the mechanism of
the Mitsunobu reaction you'll see what I mean -- I would make sure that your
pot doesn't have a prayer of hitting pH 7.0 or below as a main prerogative to
make your step go as smoothly as possible.

Hope that helps!


PS: (But you, of course, can't have too much base or the Ph3P-Br won't be
enough to really form at all and last enough to do what you want). Good luck!

"The nature of the truth is fundamentally biased by the nature of our
      --C.J. Gorman (from personal email greeting)
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