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) is added bis(tricyclopentylphosphine)benzylidene ruthenium (IV) dichloride (1.49 g, 2.01 mmol) and the reaction mixture is stirred at room temperature for 16 hours. The solvent is removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7) provides 2.48 g (78% y, >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