The Goal
Your goal is to convert 4-methylvaleric acid (3) into the single
enantiomer of the chiral aldehyde 8 (numbers correspond to
the journal article). To assist you in this endeavor, you will receive
0.500 g of the chiral auxiliary shown below. Notice that your journal
article uses the oxazolidinone with R=isopropyl. You will need to
account for the difference in molecular weight, but the rest of the
chemistry will be the same.

The Challenge
You have all the information you need in the literature article. You
will have to adjust for the different auxiliary and for the smaller
scale. This must be done before you walk into lab. Planning
is everything. Groups that continually lose time in lab from poor
planning will be assessed accordingly. On the other hand, obtaining
compound 8 is not absolutely necessary for success--if your
lab work is well-planned and effective, if all the compounds along
the way are obtained in reasonable yield and in high purity, you have
exhibited the behavior of a conscientious research chemist, which
is the ultimate goal of this experience.