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Topic: Synthesis of aldol  (Read 3504 times)

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Offline poorstudent83

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Synthesis of aldol
« on: September 18, 2009, 06:39:31 AM »
Hi guys, I'm trying to work out a mechanism for the synthesis of an aldol from the acid catalysed reaction of an aldehyde and a diene (see attached file). I understand that the Lewis acid protonates the aldehyde resulting in the aldehdye being more reactive towards the diene. What I don't understand is what happens next! I know the silyoxy group is a good leaving group....any help would be greatly appreciated!!
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Offline sjb

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Re: Synthesis of aldol
« Reply #1 on: September 18, 2009, 07:26:36 AM »
It's not really just a diene though, is it? Perhaps look into silyl ketene acetals, or similar?
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Offline poorstudent83

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Re: Synthesis of aldol
« Reply #2 on: September 22, 2009, 08:23:12 AM »
Would I be right in thinking it's along the lines of the Mukaiyama Aldol Addition mechanism?
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Offline sjb

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Re: Synthesis of aldol
« Reply #3 on: September 22, 2009, 12:27:27 PM »
I think so, mind you I'm not fully up on names to be honest ;)
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