Department of Chemistry and Biochemistry , University of Colorado , Boulder , Colorado 80309 , United States.
J Org Chem. 2018 Sep 7;83(17):10487-10500. doi: 10.1021/acs.joc.8b01516. Epub 2018 Aug 6.
Chiral 1,2-amino alcohols are privileged scaffolds with important applications as drug candidates and chiral ligands. Although various methods for the preparation of this structural motif have been reported, these methods are limited because of the use of precious metals and ligands. Here, we report a practical and high yielding synthesis of chiral 1,2-amino alcohols using arylglyoxals and pseudoephedrine auxiliary. This reaction is catalyzed by a Brønsted acid and provides morpholinone products in high yields and selectivities. The morpholine ring was converted into 1,2-amino alcohols in a two-step protocol.
手性 1,2-氨基醇是一种重要的药物候选物和手性配体，具有重要的应用。尽管已经报道了各种制备这种结构基序的方法，但由于使用了贵金属和配体，这些方法受到限制。在这里，我们报告了一种使用芳基乙二醛和伪麻黄碱助剂的实用且高产的手性 1,2-氨基醇的合成方法。该反应由布朗斯台德酸催化，以高产率和选择性提供吗啉酮产物。通过两步法将吗啉环转化为 1,2-氨基醇。
