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Topic: boc protected amines and allyulic chlorides....  (Read 3980 times)

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Offline alphahydroxy

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boc protected amines and allyulic chlorides....
« on: May 04, 2007, 06:18:09 PM »
Can anyone help me out?

I'm looking for a procedure in which a Boc-protected amine can attack an allylic chloride in an SN2 or SN2' manner as shown in the scheme attached?

I've tried NaH in THF, t-BuMgCl and CsF/Si(OMe)4 and none of these work...

any ideas from you bright sparks?  :)
« Last Edit: May 05, 2007, 04:07:07 AM by alphahydroxy »
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Offline kiwi

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Re: boc protected amines and allyulic chlorides....
« Reply #1 on: May 05, 2007, 12:31:53 AM »
no scheme... have you considered KH? or changing to the corresponding allyl bromide? or going with dry DMF instead of THF? just a few ideas. something a little more crazy: people seem to love suzuki-like N-aryl bond formations, i wonder whether an allyl boronate will behave similarly?
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Offline alphahydroxy

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Re: boc protected amines and allyulic chlorides....
« Reply #2 on: May 05, 2007, 04:11:04 AM »
Thanks for the thoughts - I've added the scheme in now too ! :-[

I may well try dry DMF for the reaction, but I've a feeling KH/THF won't work and going to the corresponding bromide isn't an option....

Cheers for the input!
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Offline kiwi

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Re: boc protected amines and allyulic chlorides....
« Reply #3 on: May 05, 2007, 05:25:03 AM »
how about throwing in a bit of TBAI (or KI/18-c-6) for luck? works wonders on etherifications
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