From: Christopher Joseph Gorman (cjgorman$##$sas.upenn.edu)
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)
ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net
To post a message (TO EVERYBODY) send to everybody$##$orglist.net
To unsubscribe, send to everybody-request$##$orglist.net the message: unsubscribe your_orglist_password your_address
List coordinator: Joao Aires de Sousa (coordinator$##$orglist.net)
This archive was generated by hypermail 2.1.4 : Fri Jul 23 2004 - 05:07:02 EDT