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Alkene reactivity

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luscofusco:
I'm doing this exercise and it says provide reaction conditions. My idea is:

1. I can get OH on carbon 2 by a hydroboration oxidation
2. I can get OH on carbon 1 by oximercuriation demercuriation.

My question is: can I do both? If I do one I need an elimination to get the alkene again (this is just a guess, I'm not 100% sure) but isn't the H from the OH going to react faster than any of the other ones?

Since both OH are on the same plane, does epoxidation (for example with MCPBA) even work here? Because it would flip the configuration due to backside attack.

Hunter2:
Use OsO4, or MnO4-,

https://www.chemistrysteps.com/wp-content/uploads/2019/06/syn-dihydroxylation-alkene-KMnO4-OsO4-mechanism.png

https://www.organische-chemie.ch/OC/Namen/upjohn3.GIF

rolnor:
Its a chiral product so you need to do asymetric dihydroxylation.

https://en.wikipedia.org/wiki/Sharpless_asymmetric_dihydroxylation#:~:text=Sharpless%20asymmetric%20dihydroxylation%20%28also%20called%20the%20Sharpless%20bishydroxylation%29,chiral%20quinine%20ligand%20to%20form%20a%20vicinal%20diol.

Enthalpy:
For my information: how toxic is OsO4? I read astonishing data.

Hunter2:
There are a lot of toxic compounds, lice arsenic, cyanide, phosgen, a.o. If to work with it , the corresponding safety rule and features  have to be used

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