Acrolein → (2R)-Bicyclo[2.2.2]oct-5-ene-2-carboxaldehyde

Participants

Reaction Steps

To a solution of 5 (32 mg, 0.12 mmol) in CH3CN/H2O (95/5 v/v, 1.0 M) was added acrolein (501 μL, 7.5 mmol), and cyclohexadiene (238 μL, 2.5 mmol). The solution was stirred for 24 h, after which time the reaction mixture was diluted with Et2O (10 mL) and washed with H2O (10 mL). The aqueous layer was extracted with Et2O (10 mL×2) and the combined organics were dried (Na2SO4), and concentrated. Purification by silica gel chromatography (10% ether/pentane) afforded the title compound as a colorless oil in 82% yield (280 mg, 2.06 mmol); 14:1 endo:exo; 94% ee. Product ratios were determined by GLC (Bodman Γ-TA column, 75° C. isotherm, 23 psi) tr=51.0 min and 54.4 min. 1H NMR, 13C NMR, and IR data were consistent with previously reported values (Ishihara et al. (1998), supra).

Provenance & Evidence