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Topic: Sharpless AD without ligand (DHQ)2PHAL (AD-mix alpha)  (Read 1113 times)

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Offline AlphaScent

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Sharpless AD without ligand (DHQ)2PHAL (AD-mix alpha)
« on: April 03, 2019, 10:55:44 AM »
Hey all,

Can you do Sharpless conditions without the chiral ligand (DHQ)2PHAL.  Is K3Fe(CN)6 viable as a stoichiometric oxidant for the dihydroxylation without the presence of the ligand.  My quick search makes me think it should be fine.  I do not mind if I get racemic.  The mechanism based on the first page to Meyers' lecture seems to be that it should be fine.

http://hwpi.harvard.edu/files/myers/files/23-sharpless_asymmetric_dihydroxylation_reaction.pdf

Any thoughts are much appreciated!

Cheers!
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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Re: Sharpless AD without ligand (DHQ)2PHAL (AD-mix alpha)
« Reply #1 on: April 03, 2019, 10:57:31 AM »
Sorry I am just wondering about this.  My plan is to use Upjohn's conditions most likely.  Wanted to clarify my thinking.

Cheers!
If you're not part of the solution, then you're part of the precipitate

Offline rolnor

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Re: Sharpless AD without ligand (DHQ)2PHAL (AD-mix alpha)
« Reply #2 on: April 03, 2019, 11:05:11 AM »
It should be fine without the ligand. I have used OsO4 with periodate but then you get the aldehyde.

Offline AlphaScent

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Re: Sharpless AD without ligand (DHQ)2PHAL (AD-mix alpha)
« Reply #3 on: April 03, 2019, 12:23:51 PM »
Good to know rolnor.  Appreciate it.

I think I am just going to try it and see.  To be honest I was lazy today and haven't dove into the literature.  I will read the paper on the potassium ferriccyanide reaction on that Meyers' page.

Thanks again! 
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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« Last Edit: April 03, 2019, 03:48:30 PM by Mitch »
If you're not part of the solution, then you're part of the precipitate

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