Racemate of (3aR,4S,9bR)-4-(p-tolyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline

To an NMR tube was added ortho-aminobenzaldehye (7.7 mg, 0.06 mmol, 1 equiv) and homoallylic alcohol (14.6 mg, 0.09 mmol, 1.5 equiv). In a separate vial was weighed CSA (13.8 mg, 0.06 mmol, 1 equiv) which was dissolved in HFIP and CDCl3. This was then transferred to the NMR tube to yield a red solution. The reaction was monitored by NMR analysis and quenched after six hours by addition of sat. NaHCO3. The organic layer was extracted with DCM, dried over anhydrous Na2SO4 and concentrated under a stream of N2. The product was isolated by flash column chromatography 25% diethyl ether/petroleum ether.