To be complete, I wasn’t reducing an ester, it was a thioimide. It was an (OH-protected) aldol adduct utilizing a thiazolidinethione as a chiral auxiliary. We developed the conditions for the aldol addition in our laboratory. Suffice it to say we did the diastereoselective aldol addition a lot . Partial reduction of the thioimide to the aldehyde was a common next transformation, so we always had a fresh bottle of DIBAL in the fridge. I reduced 5 different thioimides this way who knows how many times as I ran through the synthetic scheme who knows how many times.
I have found this site very very helpful at many points through my journey in Org 1 and 2, but now, towards the end of org 2 I am finding it less and less useful, which seems strange since there are more and more reactions. Why are there so few reactions of carboxylic acids? carboxylic acid chemistry is the core of org 2, not to mention biochemistry. It would be really really helpful if there were more of them. Also, I think there needs to be some consistency with where reactions are placed, if they are going from a type of molecule, they should all be grouped in that grouping, or maybe have two legends so reactions can be looked up based on their reactant or product.