[rolnor]

I think you would get 1,4-addition if you mix the ketone with amine.

[sharbeldam]

Can someone just give me a reaction that I can do on carvone that once I react it with tartaric acid it gives two diastereomers? I’m so confused now

[Babcock_Hall]

Free tartaric acid might or might not work, but a diester might be better.  I would make the ketal, using the ketone group of carvone.  After separation, I would hydrolyze.

[rolnor]

I also thought of a ketal, mayby its complicated when you have the isopropylene group, this group can also react with alcohols under acidic conditions. I think you can do this without acid if you make a stannane of the tartaric ester. Then the question is, will these two diastereomeres separate in a good way? Maybe by crystallisation its possible to separate them, on silica-gel its less likely.

[sharbeldam]

By saying ketal do you guys mean adding a diol or using the diol of the tartaric acid? Cause according to the book a modification need to happen on the carvone before reacting with the tartaric acid.

[rolnor]

Then its probably wrong to make a ketal.

[rolnor]

You can reduce carvone to the alcohol and make a tartaric ester, separate, hydrolyze and oxidize. Not very easy though.
In this link you can se the reduction;

Edit; This is a bad idea, the two enatiomeres of carvone will create twoo different alcohols.

https://en.wikipedia.org/wiki/Carvone

[rolnor]

Maybe a enamine is the only way. The methyl group might hinder 1,4-addition.

[Babcock_Hall]

By saying ketal do you guys mean adding a diol or using the diol of the tartaric acid? Cause according to the book a modification need to happen on the carvone before reacting with the tartaric acid.

Do I understand correctly that the book does not specify the modification?  Can you quote what they say?

[sharbeldam]

Rolnor thank you!
Babock, i would have put the source but it is not in english, it just says there is a modification reaction (not specified) and then after it is modified it reacts with tartaric acid to produce 2 diastereoisomers that can be separated, perhaps what rolnor said is what they mean.

you guys all helped me a lot!

[sjb]

It may not even be a bond formation. but just cocrystallisation of carvone and the enantiopure acid

[rolnor]

Sharbeldam says it should be some kind of change in the carvone molecule.

[AWK]

Rolnor thank you!
Babock, i would have put the source but it is not in english, it just says there is a modification reaction (not specified) and then after it is modified it reacts with tartaric acid to produce 2 diastereoisomers that can be separated, perhaps what rolnor said is what they mean.

you guys all helped me a lot!

This is very important information that had to be provided at the very beginning. Due to the lack of this information, a few people wasted their time unnecessarily. You've been using this forum long enough to put your questions right!

[sharbeldam]

Sorry I wasn't clear in my original post, the only reason for that was that the book mentioned it's a very known method, so I believed that and thought people would just know what I'm talking about. I did imply in the first page that I needed to make something from carvone to react it with the acid, but either way I apologize AWK and thanks!