ORGLIST: a question about sakurai reaction

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From: Xi, Kai (kxi2$##$uic.edu)
Date: Mon May 23 2005 - 02:39:56 EDT


Hi,there:

    I have a question about sakurai reaction. Allyltrimethyl silane react
with aldehyde under lewis acid condition to give the homoallylic
alcohol product. If fpeople 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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