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    • 3. 发明授权
    • Making optically active alpha-hydroxy acids or precursors
    • 制备光学活性的α-羟基酸或前体
    • US5324856A
    • 1994-06-28
    • US930245
    • 1992-08-17
    • Mark C. CesaRobert A. DubbertJames D. Burrington
    • Mark C. CesaRobert A. DubbertJames D. Burrington
    • C07C51/12C07C67/03C07C59/08
    • C07C51/12C07C67/03C07B2200/07
    • Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.Also disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, the enol portion of which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) hydrolyzing the product of (1) to make a diastereomeric mixture containing .alpha.-hydroxy acids, and (3) separating by conventional physical means from the product of (2) at least one .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.
    • 公开了一种制备相对于与所述酸的羧基键合的手性C原子基本上全部为L或全部D的α-羟基酸的方法,其包括(1)将具有手性C原子的烯醇酰化物加氢羧化 基本上全部是L或全部D,与CO和水或有机羟基化合物反应,从而产生含有非对映体α-酰氧基酸或具有两个手性中心并且基本上没有对映体对的酯的反应混合物,(2)将非对映体按 常规的物理手段和(3)水解所述分离的非对映异构体中的至少一种以制备至少相对于键合到所述酸的羧基的手性C原子全部为L或全部D的α-羟基酸。 还公开了制备相对于与所述酸的羧基键合的手性C原子基本上全部为L或全部D的α-羟基酸的方法,其包括(1)将烯醇酰化物加氢羧化,其烯醇部分 具有基本上全部为L或全部D的手性C原子,其具有CO和水或有机羟基化合物,从而产生含有非对映体α-酰氧基酸或具有两个手性中心并且基本上没有对映异构体对的酯的反应混合物(2 )水解(1)的产物以制备含有α-羟基酸的非对映体混合物,和(3)通过常规物理方法从(2)的产物中分离至少一种基本上全部为L或全部D的α-羟基酸 相对于与所述酸的羧基键合的手性C原子。