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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: loves2Spl00ge on December 02, 2016, 12:03:44 AM

Title: Organocatalysis mechanism?
Post by: loves2Spl00ge 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?

Title: Re: Organocatalysis mechanism?
Post by: critzz 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?

Title: Re: Organocatalysis mechanism?
Post by: loves2Spl00ge 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?

Title: Re: Organocatalysis mechanism?
Post by: critzz on December 03, 2016, 06:43:18 AM

Yes, could you draw the mechanism you got right now?

Title: Re: Organocatalysis mechanism?
Post by: phth 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.

Title: Re: Organocatalysis mechanism?
Post by: critzz on December 05, 2016, 08:42:46 AM

Step 4) profit