Whitby group

To a stirring solution of titanium isopropoxide (2.5 mmol, 0.74 mL), Et₂O (10.0 mL), and ⁱPrMgCl (2.75 mL, 5.5 mmol) at – 78 °C, N-allyl-N-methyl-N-(3-phenyl-3-butenyl)amine (412, 201.0 mg, 1.0 mmol) was added dropwise.  The mixture was stirred at –50 °C for 1 hour, then warmed to between –40 °C and –30 °C for 5 hours.  When no starting material remained (GC analysis) the reaction was quenched by the addition of methanol (6.0 mL) and a saturated solution of NaHCO₃ (8.0 mL).  The product was extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (4 x 50 mL), brine (50.0 mL), dried over MgSO₄, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO₂, 0-100 % Et₂O:petroleum including 5 % Et₃N) afforded the title compound (12 mg, 0.12 mmol, 12 %).