The Production of Chiral beta-Aminoalcohols to be excellent catalysts for the synthesis of optically active sec-alcohols.

光学活性仲醇的合成方法有不对称酮的不对称还原法和醛的不对称烷基化法。作者于1983年发现了在β-氨基醇催化下醛与二烷基锌的不对称烷基化反应。本文首次研究了醛类烷基化反应的优良催化剂2-羟基-3，3-二甲基丁胺的合成方法。用NaBH_4在MeOH-H_2 O中还原单卤代频哪酮，再经碱处理，得到叔丁基环氧乙烷，在0 ℃下进行单溴化或单氯化反应，可获得高产率的频哪酮。这样，得到的叔丁基环氧乙烷与仲胺的N-镁盐反应，以高产率得到N-二烷基-2-羟基-3，3-二甲基-1-丁胺。利用该方法可以制备多种β-氨基醇，并利用Sharpless不对称氧化法拆分外消旋β-氨基醇，该方法是拆分β-氨基醇的一种非常有用的方法。光学活性β-氨基醇的工业化生产尚处于探索阶段。

The synthetic methods of optically active sec-alcohols are knwon that asymmetric reductions of unsymmetrical ketones or the asymmetric alkylation of aldehydes are useful methods. The author found the asymmetric alkylation method of aldehydes with dialkylzinc catalyzed by beta-aminoalcohols in 1983. For the first time we studied the synthetic method of optically active 2-hydroxy-3,3-dimethyl-butylamine which was excellent catalysts for alkylation of aldehydes. High yield production ofmonobromination or monochlorination of pinacolone was succeeded by the reaction at 0ﾟC.The reduction of monohalogeno-pinacolone was performed by NaBH_4 in MeOH-H_2O,followed by treatment of alkalline to give t-butylethylene oxide. Thus, obtained t-butylethylene oxide was reacted with N-magnesium salt of sec-amines to give N-dialkyl-2-hydroxy-3,3-dimethyl-1-butylamines in high yield. By this method a variety of beta-aminoalcohols could be prepared.Rac-beta-aminoalcohols was resolved by Sharpless asymmetric oxidation which was very useful method for resolving beta-aminoalcohols. The production of optically active beta-amino-alcohols in industrial scale is now in pending, because the demand of the products is now in step of researching.