HCID 68772872, compound → HCID 86648187, compound

Participants

Reaction Conditions

Reaction Steps

(3aS,4R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4-vinyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (2-3) (7.0 g, 42.1 mmol, 1.0 equiv) was dissolved in a freshly prepared solution of DMDO in acetone (460 mL, 0.085 M, 0.9 equity), stirred at −20° C. for 7 hours and stored at −18° C. overnight. The reaction mixture was concentrated and purified via flash chromatography on a silica gel column (ethyl acetate/hexanes) to yield desired (3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (2-4) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 5.92 (t, J=5.7 Hz, 1H); 5.75-5.71 (m, 1H); 5.17 (d, J=5.8 Hz, 1H); 4.70-4.57 (m, 1H); 2.98-2.89 (m, 2H); 2.77-2.72 (m, 1H); 2.55 (dt, J=4.8, 2.8 Hz, 1H); 1.41 (s, 3H); 1.35 (d, J=2.3 Hz, 3H).

Provenance & Evidence