| 摘要 |
PURPOSE: Provided are a water soluble chiral auxiliary (5R,5'R)-5,5'-bis(oxazolidin-2-one) and its synthetic process, thereby synthesizing 2 equivalent of chiral compounds using 1 equivalent of chiral auxiliary agent and removing high cost of chiral auxiliary agent from organic reaction products. CONSTITUTION: The water soluble chiral auxiliary (5R,5'R)-5,5'-bis(oxazolidin-2-one) is represented by the formula(1). It is manufactured by the steps of: hydrogenation debenzylating 1,4-dibenzyl-2,3-dimethylsulfonyl tetrahydroxy butane under hydrogen atmosphere of 1 atm, to prepare (2S,3S)-2,3-bis(O-methanesulfonyl)-1,2,3,4-tetrahydroxy butane; heating and refluxing (2S,3S)-2,3-bis(O-methanesulfonyl)-1,2,3,4-tetrahydroxy butane and benzyl isocyanate to prepare (5R,5R')-N,N'-dibenzyl-5,5'-bis(oxazolidin-2-on) under sodium hydride; and debenzylating (5R,5R')-N,N'-dibenzyl-5,5'-bis(oxazolidin-2-on) using liquid ammonia and sodium metal to obtain (5R,5'R)-5,5'-bis(oxazolidin-2-one) of the formula(1).
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