Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of ureas or thioureas
A technology of thiourea, X-A, applied in the direction of organic chemistry and so on
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[0183] The present invention is further illustrated by the following experiments.
[0184] use different additives
[0185] At 23 °C, in a 20 mL round bottom flask equipped with a magnetic stir bar, heating device, water and argon supply, 0.5 mmol 2-acetyl-3,5,6-trimethylhydroquinone and 0.795 mmol Table 1 The additives indicated in were suspended in 2.5 mL (23.47 mmol) of toluene. Then, 0.514 mmol of E,E-farnesylacetone was added, and finally 0.795 mmol of (S)-2-(methoxymethyl)pyrrolidine was added. The reaction mixture was then stirred at 23 °C for the time indicated in Table 1. When heated to 120°C, water was distilled off and the reaction mixture turned brown. After the indicated time at 120°C, the reaction mixture was cooled to 23°C. Then 1 mL of 2N HCl was added and the mixture was transferred to a separatory funnel and shaken well. The toluene phase was separated and washed with several 10 mL portions of water until a neutral aqueous phase was obtained. The organ...
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