Theoretically, the hydration of 1 is expected to produce five products, all stereoisomers included (Scheme 4). If the reaction proceeds via a carbocation intermediate, the expected major product Thus, in the absence of asymmetric induction, hydroboration oxidation of 1 is expected to produce a racemic mixture of the trans alcohol 5-6. Using samples of alcohols 2-6 obtained commercially, a GC method was developed to separate all the expected alcohol products. Unfortunately, the method did not show separation between the enantiomers of the anti-products 5-6. We hope to fine-tune the method to separate all diastereomers and enantiomers.