HCID 67285850, compound → HCID 68772872, compound

Participants

Reaction Conditions

Reaction Steps

(3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methyl carbonate (1-2) (1.2 g, 2.19 mmol, 1 equiv) was dissolved in anhydrous THF (22 mL) and cooled to 0° C. To the resulting mixture was added copper(I) cyanide (65 mg, 0.72 mmol, 0.33 equiv) followed by 0.7 M vinylmagnesium bromide solution in THF (7.84 mL, 5.49 mmol, 2.5 equiv). After 1 h at 0° C., the reaction was quenched with NH4Cl (10 mL) and extracted with Et2O (3×25 mL). The combined organic extracts were washed with water, dried (MgSO4), and concentrated. Purification via flash chromatography on silica gel column (ethyl acetate/hexanes) gave (3aS,4R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4-vinyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-3). 1H NMR (500 MHz, CDCl3) δ 7.25-7.55 (m, 15H), 5.94 (brd, 1H, J=0.5 Hz), 5.85 (ddd, 1H, J=7.5, 3, 17.5 Hz), 5.18 (dt, 1H, J=1.5, 17.5 Hz), 5.12 (dd, 1H, J=1, 10 Hz), 5.07 (d, 1H, J=5.5 Hz), 4.52 (d, 1H, J=6 Hz), 3.93 (d, 1H, J=14 Hz), 3.76 (d, 1H, J=14 Hz), 3.53 (d, 1H, J=7.5 Hz), 1.43 (s, 3H), 1.37 (s, 3H).

Provenance & Evidence