Natural Science Forum / Chemistry / Organic Synthesis / January 2004

How 'bout alkaline hydrogen peroxide followed by mild reduction
(sulfite, nitrite, etc.) of the peroxycarboxylate?

Dissolve your substrate in a large volume of THF-water 1:1, add
exactly 1 equivalent of LiOH.H2O solid, at room temp, and follow the
progress on TLC or HPLC. (If the hydrolysis does not go to completion,
you can add a bit more of LiOH.H2O later on.) Acidify before work-up.

If you get sideproducts with hydroxide (triflate falls off), try
acidic hydrolysis instead, something like 2M HCl mixed with THF in 1:1
ratio, at 50C.

(If you have enantiomericaly pure compound, racemization would
probably happen in this case)

hi,
u can try something funky: enzymatic---->lipase or esterase.
bye.
narcis