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4.2. General procedure for asymmetric epoxidation of
trans-chalcones and naphthoquinones
To a solution of hydroperoxide 3 (100mg, 0.515mmol)
in dry THF (3mL) under an argon atmosphere at
À20°C, n-BuLi (224lL, 0.561mmol, 2.5M solution)
was added. After 15min, enone 4 or 7 (0.468mmol) dis-
solved in dry THF (2mL) was cannulated into the flask.
At the end of the reaction, as verified by TLC, a solution
of Na2SO3 (0.5mL, 1M solution) was added and the
mixture was stirred for 10min at room temperature.
The organic phase was diluted with diethyl ether
(30mL) and then washed with water. After drying with
Na2SO4, the solvent was removed under reduced pres-
sure and the crude product was purified by flash chro-
matography (petrol/diethyl ether 99/1) to give epoxide
5 or 8 and alcohol 6. Physical and spectroscopic data
of epoxides 5 and 8 matched those reported.8,16b,20
`
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Acknowledgements
11. After 3h at room temperature, hydroperoxide 3 was
consumed showing a substantial decomposition of the
oxidant.
`
We thank Universita degli Studi di Salerno and MIUR
(Sostanze naturali ed analoghi sintetici con attivita
`
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antitumorale) for financial support.
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