[Juaqui]

Hello people,

This two molecules are supposed to be the same molecule. I got this by an Diels-Alder reaction (one is seen from a point of view and the another one is seen from another point of view). But when I apply the Cahn, Ingold and Prelog rule I get the enantiomers!!! Could you tell me what is the absolute configuration of the the pink carbons?

Thanks a lot!!!

 https://ibb.co/gtmA7q

[mjc123]

If there was an H instead of the ester side group, these would be the same molecule, as there would be a plane of symmetry down the middle of the molecule. Inserting that side group takes away that symmetry, and the molecules you have drawn are enantiomers.

[kriggy]

If there was an H instead of the ester side group, these would be the same molecule, as there would be a plane of symmetry down the middle of the molecule. Inserting that side group takes away that symmetry, and the molecules you have drawn are enantiomers.

There is another chiral center at the side chain which is same in both molecules, therefore they are not enantiomers but diastereomers.

Hello people,

This two molecules are supposed to be the same molecule. I got this by an Diels-Alder reaction (one is seen from a point of view and the another one is seen from another point of view). But when I apply the Cahn, Ingold and Prelog rule I get the enantiomers!!! Could you tell me what is the absolute configuration of the the pink carbons?

Thanks a lot!!!

 https://ibb.co/gtmA7q

Unless you get some chiral catalyst or something, the DA reaction is bound to give racemic product because the diene can approach the dienophile from both sides

[clarkstill]

Unless you get some chiral catalyst or something, the DA reaction is bound to give racemic product because the diene can approach the dienophile from both sides

But I guess in this case the chiral hydroxy-lactone might act as a chiral auxiliary/directing group, so you wouldn't necessarily get 1:1 mixture of product diastereoisomers

[Juaqui]

Thank you very much for your answers, guys. I'm going to share with you a picture where there are both the reagents and the product that I think is correct. I have to write the absolute configuration because the dieno is approaching to the dienophile from the naphthoquinone's upper face.
https://ibb.co/jzjRFL
Do you think that this product is the correct one?

Sorry about my bad English, too.

Greetings!

[kriggy]

But I guess in this case the chiral hydroxy-lactone might act as a chiral auxiliary/directing group, so you wouldn't necessarily get 1:1 mixture of product diastereoisomers

Yeah, its possible, im not sure how good directing group it will be.  Im not that experienced in this kind of chemistry, but my guts tell me that the methylene bridge should point opposite side with regards to the carboxy functionality?