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Topic: Organocatalysis mechanism?  (Read 2072 times)

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Offline loves2Spl00ge

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Organocatalysis mechanism?
« on: December 02, 2016, 12:03:44 AM »
I'm stuck on how this mechanism should start. My gut is saying the primary amine attacks either the aldehyde carbonyls or the CH2 pi orbitals. Any suggestions?
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Offline critzz

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Re: Organocatalysis mechanism?
« Reply #1 on: December 02, 2016, 07:54:08 AM »
Start out on the condensation of the primary amine and the shorter one of the two aldehydes. From there on you could try and figure out the mechanism, using arrow-pushing of electrons.

Have you learned about the Pictet-Spengler and Sakurai reactions yet?
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Offline loves2Spl00ge

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Re: Organocatalysis mechanism?
« Reply #2 on: December 02, 2016, 02:02:36 PM »
We didn't go over those two reactions, but I did google them, and it made things much clearer. Will the step after the pictet-spengler reaction be an intramolecular sakurai?
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Offline critzz

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Re: Organocatalysis mechanism?
« Reply #3 on: December 03, 2016, 06:43:18 AM »
Yes, could you draw the mechanism you got right now?
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Offline phth

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Re: Organocatalysis mechanism?
« Reply #4 on: December 03, 2016, 07:52:48 PM »
Step 1) list the possibilities by making an educated guess what plausible mechanisms are.
Step 2) ???
Step 3) choose the one that leads to the product.
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Offline critzz

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Re: Organocatalysis mechanism?
« Reply #5 on: December 05, 2016, 08:42:46 AM »
Step 4) profit
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