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Topic: Stereochemistry of Product  (Read 2107 times)

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Offline Corndog88

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Stereochemistry of Product
« on: October 06, 2014, 02:06:29 PM »
Hi everyone,

I need help with this problem, I'm attaching a picture of the reactants. I need to draw the product with correct stereochem, and I'm having trouble. I know this is a standard Diels-Alder mechanism, just need some insight...

THANKS!!!
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Offline discodermolide

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Re: Stereochemistry of Product
« Reply #1 on: October 06, 2014, 02:37:44 PM »
Are you sure this is a Diels-Alder reaction?
Can you draw the product?
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Offline Corndog88

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Re: Stereochemistry of Product
« Reply #2 on: October 06, 2014, 02:49:01 PM »
I think??
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Offline discodermolide

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Re: Stereochemistry of Product
« Reply #3 on: October 07, 2014, 12:07:26 AM »
I think you'll find that the 1,3-dipolar cycloaddition gives products where the substituents are all on the same side of the molecule:
[H][C@@]1(CCC2)[C@@]2([H])[C@H](C(OC)=O)N(C3=CC=CC=C3)[C@@H]1C(OC)=O

Note the SMILES engine gave this a chiral flag, it's not chiral.
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Offline Corndog88

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Re: Stereochemistry of Product
« Reply #4 on: October 07, 2014, 06:25:10 PM »
Thank you!  ;D ;D ;D ;D
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