reducing only one ketone group

[Bromo_DragonFly]

hi friends

 

Q :

has any one heard of reducing only one ketone when two are neighbored next to each other ?

i want to know if it's possible and whether it has been done before or not.

if anyone knows something about it (patents or anything) I'd be thankful to hear about. in fact i want to guess the mechanism for it.

 

I'm asking because it happened in my reaction pot in a yield of around 55%. maybe it's some new stuff. I don't know. I hope it is.

picture is what I've done :

 

[hypervalent_iodine]

I haven't performed anything like it myself, but I can't see why it wouldn't have been done before (certainly it's been done with enzymatic reactions in the past). Your yield of ketone seems quite high, though; I would normally expect to see a higher yield of the alpha-hydroxy ketone. What was your yield of the other reduction product(s)? Anyway, if your compound is asymmetric and has carbonyls of varying reactivity, you could get regioselectivity by controlling the rate of addition and equivalents of reagent added. The extent of regioselectivity would depend on how different the reactivities are.

 

Have you done a SciFinder search at all? You may find something similar there.

[Bromo_DragonFly]

the similar stuff i find is for amides.

like those reductions done with metal catalysts.

but my reaction is not from an amide.

 

how can i get more specific info about enzymatic reactions, their mechanisms .etc ?

i mean the ones similar to this kind of reduction.

 

thanks.

Edited July 3, 2013 by Bromo_DragonFly