HCID 86588255, compound → HCID 11243997, compound

Participants

Reaction Steps

To a solution of (2R)-2-{2-[1-propenyl]phenoxy}-3-butenyl 4-methyl-benzenesulfonate (3.61 g, 10.1 mmol) in dichloromethane (100 mL) was added bis(tricyclopentylphoshine)benzylidene ruthenium(IV) dichloride (1.49 g, 2.01 mmol) and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7) provided 2.48 g (78%, >97% ee) of (2R)-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate as a pale green crystalline solid. [α]D25=+175.12 (c 9.99 in methanol, >97% ee); Rf=0.40 (silica, ethyl acetate:hexanes 3:7); Anal. Calcd. for C11H16O4S: C, 64.54; H, 5.10. Found: C, 64.85; H, 5.05.

Provenance & Evidence