[AlphaScent]

I have just started graduate school and am realizing that there is some things I need to brush up upon.

The following reaction was proposed to me and I was told to give the product paying close mind to stereo chemistry.

At first it seems to be the second part of hydroboration.  Only there is no reagent given to produce the anti-diols.

My first thought is that the double bond could be epoxidized.  What am I not seeing. 

Hints as opposed to a direct answer would be better for me in this situation, much appreciated!!

Cheers!

[Babcock_Hall]

Assuming that you could create an epoxide, what sort of chemistry could epoxides do?

[AlphaScent]

An epoxide can accept a nucleophile at the least substituted position.  Hydroxide is too strong of a base for it to react nucleophilically.  I believe I have to look at the electron deficient enone and see what kind of chhemistry can happen there under these conditions.

I think it is epoxidation at the alpha beta unsaturated position.

Along the lines of a Julia-Colonna epoxidation.

[Babcock_Hall]

An epoxide can accept a nucleophile at the least substituted position.  Hydroxide is too strong of a base for it to react nucleophilically.  I believe I have to look at the electron deficient enone and see what kind of chhemistry can happen there under these conditions.

I am not sure I agree with your second sentence, but I have no direct experience.  I did consult an organic chemistry textbook, which indicated that epoxides may be opened by hydroxide at elevated temperatures.

[AlphaScent]

Once I have a reference I will post it.

I do agree with you that it can open an epoxide to the diol.  I was talking to another student and he showed me quickly notes from the previous semester about this reaction.  I am going to email him and see if I cannot get a reference.

I think my professor is looking for this specific epoxidation because she gives no temperatures in any of the problems.

For instance she gives a Rubottom oxidation problem where the LDA can attack and give the alpha proton at the kinetic or the thermodynamic position and since no temperature was given I just put both answers.

Be back soon.

[AlphaScent]

Not a reference but a good thought..

http://www.chemtube3d.com/DoubleBondGeometry-PeroxideAddition(E).html