ORGLIST: a question about sakurai reaction

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From: Xi, Kai (kxi2$##$uic.edu)
Date: Wed May 18 2005 - 16:32:57 EDT


Hi,there:

    I have a question about sakurai reaction. people always use
allyltrimethyl silane with aldehyde under lewis acid condition to do
the reaction to get the homoallylic alcohol product. If people add an
alkyl group on the terminal position of the double bond of the
allyltrimethyl silane, will this reaction go very slowly? If the alkyl
group is methyl, it is ok. But is it still ok if the alkyl group is
propyl or even including heteroatom, I mean more hindered? will this
reaction have to need room temprature?

Thanks a lot!

Skywalker

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