ORGLIST: imine refuses phosphite

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From: Witek Mozga (mozga$##$trimen.pl)
Date: Sun May 20 2001 - 13:43:38 EDT



Dear all,

I have been trying to conduct addition of dimethyl phosphite to the
N=C double bond of imine (Kabatschnik-Fields reaction).
However the substrates (amine and aldehyde) are very
hindered. Nevertheless the imine has been formed.
Unfortunately I cannot make phosphite to add to it. I`ve
tried different conditions involving a Lewis acid as well as base
catalysts and generation of phosphite anion with Na. Everything failed.
Do you have any idea what chemistry I could use to perform the
successful addition of phosphite to very rigid and hindered imine?
Maybe some of you could give me any advice?

With best regards

Witek



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