ok, time for _Organic Syntheses_ roulette. with the new rule, choosing a pseudorandom four-digit number and then searching orgsyn.org for it!
and the number is 2564 - heh well at least we know it's divisible by 4
ooh, what a curious one this time
http://orgsyn.org/demo.aspx?prep=v92p0320
direct *asymmetric* alpha-hydroxymethylation of aliphatic aldehydes. here, isovaleraldehyde (or, if you like, 2-methyl-n-butyraldehyde) is converted to the formaldehyde acetal of the (R)-hydroxymethylated aldehyde
(cont'd) here, an oxidative hydrolysis is carried out with sodium chlorite (a popular mild aqueous oxidant for a number of organic reactions) buffered with monobasic sodium phosphate in t-butyl alcohol. that gives the alpha-hydromethylated isovaleric acid, rather than the aldehyde.
neat! working with formaldehyde is kind of a bummer and I wonder if there's any way to jigger the synthesis to use sym-trioxane instead.
the reaction is carried out with formalin (the standard 37% solution of formaldehyde in methanol that is the usual reagent form of formaldehyde) in the presence of toluene, a pH 7 buffer, and a chiral phosphine catalyst, (S)-1,1-diphenylprolinol trimethylsilyl ether, a catalyst undoubtedly synthesized from naturally occurring amino acid proline
presumably, plain mild hydrolysis of the resulting acetal of the hydroxymethylated aldehyde would yield the aldehyde itself, but (cont'd)