Additional References:Footnote 16: Sparteine has been used as a ligand for palladium-catalyzed allylic substitution reactions and olefin polymerization reactions. (a) Trost, B. M.; Dietsch, T. J. J. Amer. Chem. Soc. 1973, 95, 8200. (b)
2000, 33, 715.Material and Methods. Unless stated otherwise, reactions were performed in flame-dried glassware under a nitrogen or an argon atmosphere, using freshly distilled solvents. All other commercially obtained reagents were used as received. Reaction temperatures were controlled by an IKAmag temperature modulator. Thin-layer chromatography (TLC) was performed using E. Merck silica gel 60 F254 precoated plates (0.25 mm). ICN Silica gel (particle size 0.032-0.063 mm) was used for flash chromatography.Analytical chiral HPLC was performed on a Chiralcel OJ, AS, or OD-H column (each is 4.6 mm x 25 cm) obtained from Daicel Chemical Industries, Ltd. Analytical achiral GC was performed using an Agilent DB-WAX (30.0 m x 0.25 m) column. Analytical chiral GC was carried out using a Chiraldex B-DM column (30.0 m x 0.25 mm) purchased from Bodman Industries. Commercially available racemic alcohols in Table 3 (entries 1, 2, 3, 5, 7, 8, and 9) were purchased from the Sigma-Aldrich Chemical Company, Milwaukee, WI. Non-commercially available racemic alcohols used in Table 3 (corresponding to entries 4, 6, and 10) were prepared as previously described. 1 Commercially available samples of enantiopure alcohols for analytical comparison purposes (entries 1, 4, 7, 8, and 9) were purchased from the SigmaAldrich Chemical Company, Milwaukee, WI. Non-commercially available enantiopure alcohols prepared 1 (a) Ruble, J. C.; Latham, H. A.; Fu, G. C.